Many people hide behind the easiest communication channel when they negotiate for higher pay. This usually means sending an email. The problem is that you cannot control how the reader feels or interprets your tone. If a CEO is already stressed at the airport, they might see your request for more money as a sign of greed.

I might email you my demands. The problem with that is I can't control tone. If I push back and the CEO that reads it is in the airport security line and they read it, they might be like, that bastard wants more money.

A common fear is that asking for more will make you look greedy or cause the deal to fail. However, negotiation does not have to be aggressive. Jacob suggests a softer approach by simply asking if there is a chance for a little more money. This is not greedy when compared to the revenue companies generate.

To negotiate effectively, you should focus on the specific problems you can solve. Companies have significant leverage because they know the market rates and what others are making. You can balance this power dynamic by understanding and communicating the value you create.

The simplest advice is, what's the chance there could be a little more? That's not greedy at all. The philosophy is to make it very clear to the company, here's the pain I will solve for you, and here's why it's worth paying me this much more.

Many people leave significant money on the table because they fear appearing greedy or confrontational. Jacob explains that even a simple, non-aggressive pushback can result in a 20% improvement on an initial offer. This applies to both entry-level roles and million-dollar executive positions. While many people see salary bands as absolute, those who challenge authority in a collaborative way often win more. Professional negotiation can often lead to a 40% increase, and it is even possible to break through supposed salary caps.

The simplest advice that I can give you is, what's the chance there could be a little more? That's not greedy at all. It's just a simple ask. And even that can lead to a 20% or 30% increase.

Jacob notes that product leaders, engineers, and designers tend to negotiate more poorly than extroverted marketers. This is frustrating because product work often defines a company's success. He encourages employees to realize that companies usually extract much more value from them than they pay out, often at a ratio of 10 to 1 or even 100 to 1. Understanding this value exchange helps build the confidence needed to ask for more. Negotiating is simply a way to make the exchange more fair, especially since W2 employees are taxed so heavily.

A company is extracting much more value out of you, naturally. Like 5 to 1, 10 to 1, 100 to 1. If you understand that value exchange, you can have that conversation with confidence.

Attracting and keeping top talent is essential for any organization. This is especially true as the speed of innovation continues to accelerate. It is expensive to replace high performers. Replacing a key employee can cost hundreds of thousands or even millions of dollars in lost intellectual property. Jacob challenges hiring managers to view negotiation as a collaborative value exchange rather than an adversarial process. When a candidate understands what is important to a founder, both parties can reach terms that benefit everyone.

This is a myth about negotiation. That it is adversarial. What I teach is how can we be more collaborative? So the conversation is, look, can you help me understand what's important to you, the value that this work will drive? And then naturally we'll come to terms that make a little bit more of a value exchange.

Jacob suggests getting creative with performance incentives. This might include milestone triggers instead of just focusing on a base salary. Candidates can advocate for extra stock or cash if the company hits specific growth targets. These structures ensure that employees have skin in the game. They are more likely to stay for the long term. To build a competitive organization, you must be competitive with pay. You must be willing to reward success when it happens.

Executive compensation negotiations often involve massive stakes. In some instances, a team might negotiate an increase of 10 million dollars to prevent a company from losing hundreds of millions in market value. If a CEO makes public promises about key talent, losing those individuals to competitors can cause stock prices to drop. Paying a premium to retain critical staff is often a small price to pay compared to the cost of business disruption.

Jacob Warwick uses a fingerprintless strategy to help executives navigate these high-stakes discussions. Unlike Hollywood where agents negotiate directly, corporate leaders usually avoid middle mediators to maintain their sense of authority. Instead, Jacob acts as a behind-the-scenes advisor. Every email and conversation is planned together before the executive speaks. This method keeps the leader in the driver's seat while ensuring every word is polished and strategic.

In Hollywood, you have an agent negotiate on your behalf and they are serving as that middle mediator. That's not common in corporate America right now. If that happens, it almost dilutes the leadership and presence of the executive.

A key part of this strategy is intentionally slowing down the process. Haste creates unnecessary risk. Taking a few days to respond to an offer is not about being difficult or manufacturing fake urgency. It shows that the executive is thoughtful and that their time is scarce. This slower pace allows for better information gathering and more calculated decision-making.

Haste equals risk. As you slow down, we want to take a couple of days to respond. Not to be a jerk or to manufacture some fake urgency, but it shows a little scarcity and thought process to your time and we get to calculate and collect information through the process.

Negotiation begins much earlier than the actual conversation about a job offer. It starts with your public reputation and how you are perceived on platforms like LinkedIn. Jacob notes that even small details like the quality of a headshot can signal your professional value. If you are positioned as a commodity, you will be treated like one.

Everything you communicate starts to serve as that value chain across the board.

It is often better to share less information publicly so you can steer the narrative during a direct conversation. This prevents recruiters from anchoring your value to what you did years ago. A common mistake is trying to negotiate via email. You cannot control your tone or how the message is received. A CEO might read a perfectly worded email while they are stressed at the airport and only see a demand for more money. Video calls or in-person meetings allow for reading body language and adjusting the tone in real time.

If you catch them at the wrong time, you have no control over how it is received. So it is always better to have at least a video call if not in person.

Negotiating through recruiters can lead to a game of telephone. The recruiter may not convey your reasoning or tone accurately to the decision-maker. Instead, you should speak directly to the person who controls the budget and has skin in the game. While this might feel uncomfortable, Jacob argues that running toward that discomfort is where professional growth happens.

Negotiation should happen over a video call or in person rather than through email. It is important to speak with the person who has the most skin in the game regarding finances and budget. Jacob explains that many deals are closed on a golf course rather than in a boardroom because it moves the conversation into a different element. This is known as home field advantage. When you go to a company office, you are out of your element and may not perform your best.

Controlling the timing of the conversation also provides an advantage. If a CEO wants to meet at a time that does not suit you, it is okay to say you are unavailable. You should know when you are strongest during the day and schedule meetings for those hours. Saying no creates a rubber band effect that makes you more attractive. It communicates scarcity and shows that you will not be pushed around.

These sound like minor things to consider, but the body language and the tone and the collaboration and the energy starts to flow more naturally when you do. This is all behavioral psychology.

Jacob notes that taking a walk during a meeting can change the entire mood. Instead of sitting across from someone in a confrontational way, you are walking side by side. This makes it feel like you are solving a problem together. Even if you are not applying for a C-suite role, you can still try to pull the conversation out of the office to a more neutral place like a coffee shop. This helps build a stronger relationship and makes it more likely that you will get what you want.

Negotiating a job offer for a senior role is a difficult process. When a recruiter sends an offer with a $300,000 salary and equity, many candidates feel pressure. This fear is common when thinking about whether to ask for more. It is especially true for roles at startups backed by venture capital or private equity.

It is very scary to push back and say you want more. How do you open up a conversation where you plan to ask for more if you are meeting in person? That feels so scary.

Choosing the right phrases for the first email reply is a critical step. Knowing how to start an in person conversation about pay is a major hurdle for many people at this level.

When you receive a job offer, start with gratitude and enthusiasm. Even if the numbers are lower than expected, projecting confidence that the deal will get done helps the employer feel secure. Taking a few days to process the offer is standard practice, especially for executive roles where legal or financial advisors might need to review the details. By signaling that you are looking forward to working together, any later requests for adjustments appear reasonable rather than confrontational.

The point is you have to sell that the deal is going to be done, which helps them feel like it is going to move forward regardless. Any ask that you make is not going to be egregious.

Negotiation often involves anchoring higher to achieve better results. If an offer feels light, Jacob suggests being honest about your discomfort and then waiting for the employer to respond. Questions about the salary range and performance expectations for the top end of that range can reveal more opportunities. In some cases, top talent can even restructure a role entirely. If you bring more horsepower than anticipated, a company might up-level a senior director position to a VP role to accommodate your value.

What is the chance we can come in and restructure the compensation for the type of talent we are bringing in here?

This approach has led to significant compensation increases, sometimes doubling the initial offer by shifting the role level within the organization. While this might seem specific to high-level moves, the underlying principle of pushing for more based on the value provided applies across different career stages.

Negotiation often involves finding the ceiling rather than just settling for a middle ground. If you are a senior professional, you should avoid anchoring with a specific number too early. Anchoring creates a ceiling that limits your potential earnings. Instead, use soft pushback like asking if there is a bit more room in the budget. This keeps the conversation open and allows you to discover what the other side is actually willing to pay.

I typically don't want to re anchor with a number because you should ever be so sure of what you're worth that you wouldn't accept more. When you anchor, that's the ceiling. And what often happens is naturally they want to split the difference.

Lazy negotiating happens when parties simply split the difference. Jacob shares an example of a writer who settled for a million dollars because the parties met in the middle. However, they never actually found the ceiling of what the studio was willing to pay. If the potential value of a project is high, you should push for performance based triggers. For example, a contract could include bonuses for hitting specific milestones or achieving certain levels of success. This shifts the focus from a flat fee to the actual value you create for the company.

Professional negotiation tactics rarely translate well to personal relationships. Jacob notes that spouses who are familiar with his work can easily spot his techniques. If he tries to use a specific framework at home, his wife immediately shuts it down because she knows exactly what he is doing. Using these methods with a partner who hears you on the phone all day is generally a bad idea.

Toddlers are terrorists. I haven't figured that one out. I resort to bribes, and maybe that is a little Machiavellian on the toddlers. You can be out of your mind working on that. But I don't recommend it with your spouse.

Toddlers present an even greater challenge than spouses. They do not follow the usual rules of logic or bargaining. Jacob admits that he often abandons his professional strategies in favor of simple bribes when dealing with children. The host shares similar experiences where children will counter an offer with an even higher demand regardless of the situation. For example, offering a child one item might lead them to demand five, and then ten, simply to see what they can get if you are desperate for them to go to sleep.

The dynamics of salary negotiations change as a career matures. Early in a career, recruiters often push for a specific number because they view the hire as a commodity. As you move up the ladder, top recruiters focus more on value creation. Jacob suggests that you should avoid talking about money until you are closer to an offer. This ensures you understand the scope of the role before setting a price.

If a recruiter insists on a number, Jacob recommends asking for their budget first. Many people find it uncomfortable to say no or push back during these conversations. However, revealing your current salary too soon can limit your potential earnings.

I didn't want to tell them I was making 14 dollars an hour. Instead I said, what did you have in mind? And they said, oh, we're looking at 110 to 130. I went from 14 an hour to 120,000 dollars a year in a single jump, just like that.

Jacob used this exact strategy to transform his own life. When he was underpaid as a marketing director, he refused to share his hourly rate. By letting the recruiter name a range first, he jumped from 14 dollars an hour to a 120,000 dollar annual salary in a single month. This experience shows why it is essential to focus on the value of the role rather than your past earnings.

Power in negotiation stems from the ability to say no. This dynamic shifts when you have an immediate financial need. Jacob notes that it is often easier to find a job when you already have one because your basic financial needs are met. This allows you to negotiate with more confidence. When someone is out of work for a long time, their identity can feel stripped away. People often identify strongly with their job titles. This discomfort leads people to give in to demands just to end the pain of being unemployed.

If you have the ability to say no, you have infinite power. The nuance changes when you don't have a job and you need to pay your mortgage. You might answer differently because you want something right now. This isn't to shame somebody who's feeling that way.

Pushing back during the hiring process provides insight into a company's culture. If a recruiter reacts poorly to a polite boundary, it signals how they might treat you later. Jacob suggests a psychological technique to handle these moments. You can thank a recruiter for being an advocate and for respecting your decision not to share salary figures yet. This gives them a positive reputation to live up to. It makes it harder for them to push back aggressively.

I want to thank you for being an advocate for me and for respecting that I won't share compensation figures right now. I appreciate that. And then they're trapped. They have to say they don't respect you or they have to say it makes sense.

There is also value in continuing an interview process even if the salary seems too low. Treating these conversations as practice builds the skills needed to negotiate larger offers later. This practice can make a massive difference in career earnings over time. If a role is clearly not a fit, you can still be helpful by recommending other candidates to the recruiter.

When a job offer comes in for a senior role but the responsibilities actually reflect a director level, it is important to address the misalignment. You can tell the employer that the role does not match where you are headed and offer to introduce them to someone who is a better fit. This approach keeps you helpful while ensuring you do not accept a position that undervalues your skills.

Would you like me to make an introduction to somebody that's a better fit so you still get to help them? You remove yourself and then sometimes they say no, actually, we do want the role to be more senior. We're going to extend for you.

Jacob shares that his first VP role resulted from turning down a content manager position that paid 70,000 dollars. Six months later, he landed a VP role for a quarter million dollars with the same company. This shift happened because he did not say no too quickly and allowed the negotiation to progress several levels up the food chain.

My first VP role came out of turning down a content manager position for 70,000 and six months later I landed at VP for a quarter million. That was my first realm into VP. The initial offer was for content manager, so they came three, four levels up the food chain.

Most people do not perform the job described in their official job description. There is almost always a layer of undocumented work that only becomes clear during the interview process or after starting the role. This mismatch makes it risky for candidates to fixate on a salary number too early. When you anchor to a benchmark based on a job title, you limit your ability to negotiate when the actual scope of the work expands.

They scope creep the role. They talk about how they want a senior hire. They get you excited about it and then they give you the offer and it is actually 20 percent under the number you originally shared. Then you say this looks like a director role and I want more. And they say but you said you only wanted this amount. Now they are using a number against you.

Jacob highlights that companies often add more responsibility during the hiring process, such as leading additional teams or managing new departments. If you have already provided a salary expectation based on the initial description, it becomes difficult to justify a higher number later. It is better to show curiosity about the actual problem the company needs to solve before discussing compensation.

Jacob suggests that product engineers and designers should approach interviews like a sales conversation. A high-level hire is essentially an enterprise solution worth hundreds of thousands or even millions of dollars a year. In a typical B2B deal, it takes months to develop relationships, find champions, and understand what value can be created for each person involved. You do not just pitch a price or a past history right away.

You are an enterprise solution, a consulting solution that is several hundred thousand dollars, if not millions of dollars a year if you were to sell that product into an organization. Think enterprise B2B deals. It would take you 18 months to develop the relationships and close that deal. You have to develop champions in the organization. You have to understand what value you can create for each of those people so that they can advocate for you.

The goal is to turn the interview into a discovery process. Instead of starting with a recap of your past, which puts you on the defensive, try to pivot toward a brainstorming session or a consultation. This allows for a two-way exchange where both parties explore how to create value together. Many interviews feel like an interrogation, but asking if the interviewer is open to a brainstorm instead can change the entire dynamic for the better.

Too many interviews start with tell me about yourself, tell me about this stuff in the past. If you're talking about your past, you're on the back foot and you're losing that conversation. You're the one revealing information. You're not getting anything. We instead want to have a conversation and say, look, some of the best interviews I've always had felt a little bit more like consultations or brainstorming sessions. Are you open to having a chat like that today?

Effective negotiation begins with deep discovery. Jacob suggests starting by clarifying why you are in the room. You should label the challenges the other party faces. This might include product issues or the need to move faster. By asking if you missed anything, you encourage them to reveal more information. This process is like a SWOT analysis. It helps you find the hidden problems in an organization. You want to understand where the failures are and what is at stake.

I want to ask all these discovery questions. They're like, oh, look, it's a $10 million problem where we've gone through five different PMs in six months, and you're starting to understand where the dirty laundry in the company is.

After finding the pain points, you can sell the vacation. This means helping the person visualize a future where their problems are solved. Ask them to imagine a board meeting six months from now where they feel proud because the churn is gone. This exercise removes their stress. It makes you the only person they can imagine working with. You become the partner who leads them to a better situation.

You must also understand how your work impacts other teams. Jacob notes that staying in a bubble limits your value. You should learn the motivations of people in marketing and other departments. When you interview for a role, treat it like a value exchange. Do not just list your past deeds. Act as if you already have the job. Think about who you would introduce them to or how you would solve their problems today. This shifts the focus to the future value you provide.

If you already had the job, who would you introduce him to? If you already had it, the deal's already signed. So put yourself in the position that you're already doing the job. That's why an interview process, if you treat it like you're consulting, you're doing a value exchange.

Sales often depends on creating immediate value instead of just promising it. In one instance, a client won a deal by pre-scheduling a lunch with Steven Spielberg. Other agencies focused on their past achievements and media tours. This client focused on making a specific dream a reality right in the room. This shift in mindset involves identifying a problem and starting the work before the contract is even signed.

They lost because we sold a vacation and we made it a reality right then and there. And the value is clear.

Jacob uses a similar strategy during phone calls. He listens to who a person needs to meet and sends a text introduction immediately. This creates a reciprocity imbalance. The potential client sees the value before the call ends. It shows that he has the resources to support them regardless of whether they sign a contract.

What I want to do is show that I have the resources to support them whether they sign a contract or not.

Controlling the narrative is a vital part of navigating professional power. Jacob explains that you can influence how others describe you by planting specific ideas during a conversation. For example, asking someone what they will say about you to a friend forces them to frame your value in their own words. This technique ensures that you control the message people share when you are not in the room.

I want them to perpetuate a specific narrative. Some people might see this as manipulative, but this is just how power works. You have to control what others are saying about you to navigate your net worth and negotiate for power.

A common mistake in interviews is waiting for feedback via email. Jacob suggests asking for a status check while still on the live call. By asking if the interview felt like a slam dunk or where the gaps are, you create an opportunity to fix concerns immediately. It is much harder for someone to give a vague rejection when you are speaking with them in person.

I want to understand where those gaps are so I have an opportunity to address them. I have to do it while we are live in person because you cannot deny me in that moment without it being awkward.

Lenny points out that hiring managers are looking for people who can solve their specific problems. If a candidate identifies challenges like high churn or poor onboarding and offers solutions, they become an essential asset. The key is to deliver on those promises once you secure the role.

Reputation is everything when navigating a new role. It is important not to push so far outside of your comfort zone that you cannot deliver on your promises because that reputation will follow you. You should also avoid being too certain about specific solutions, like fixing an onboarding flow, before you truly understand the problem. Often, the perceived issue is not the actual priority for the business.

The more you slow down the process, the more you fight back about the manufactured urgency of us needing to get into that role sooner, the more information you're going to understand about that company and how you could really help.

Jacob suggests that candidates often get so caught up in the job description that they fail to ask the questions necessary to understand deeper organizational problems. Instead of simply trying to negotiate a bigger piece of the existing pie, the goal should be to work with the company to expand the pie so everyone gets a larger slice. This approach requires transparency and a commitment to under-promising and over-delivering.

Jacob helps people gain confidence by acting as a hype man and reminding them of their existing success. Many high level professionals have already made choices that put them in the top percentile of earners globally. Their track record is proof of their ability to achieve big things. To make the job search feel more manageable, Jacob reframes the process using the specific professional language his clients already understand.

For a sales leader, the job search is an enterprise sales process. For a marketer, it is a lesson in positioning and market research. For those in product, it is about understanding user demands and eliminating friction for the buyer. In this context, the buyer is the hiring manager or the CEO.

How does that look in your job search? Well, what does the customer want? Who is your buyer? The buyer is the hiring manager. Maybe it is the chief product officer, maybe it is the CEO. What do they care about? When you are doing it for a company, you know which customers to interview. You need to interview lots of CEOs. You are now interviewing your customers, you are understanding their needs, now you are designing solutions for their needs. How do you make it as frictionless as possible so it is a no brainer?

People often feel they need a specific extroverted personality to succeed in a job search. Jacob encourages candidates to avoid trying to be someone else and instead apply their authentic skills to their career. While managing a career this way may feel difficult and unpolished at first, much like writing early product documents, it eventually becomes second nature with practice.

Position yourself the same way you would position a product. Understand the employer's pain points and present yourself as the solution. Most people spend interviews talking about their past. This might build credibility, but it does not solve problems. You end up repeating your story to person after person without any growth or progress.

Jacob suggests making the process frictionless by leading the narrative. Focus on the current needs of the company. Ask what problems they have and what they have tried so far. This takes the pressure off the interviewer and lets you collect information while building value.

How do we make this frictionless? I want to make it cognitively easier for you to have a conversation with me by leading. Why am I here? What are the problems you have? I suspect it is this. What have you done about it? What would it look like if we solved it now? I am taking so much of the pressure off of you. I am controlling the narrative and I am focused on creating as much value as possible.

Jacob also recommends turning interviewers into coaches. Ask for advice on how to handle the next person in the hiring process. If an interviewer coaches you, they become invested in your success. They are more likely to speak highly of you to the next person. This strategy builds momentum and makes the transition between interview rounds much smoother.

I want to put you in a position to be a coach because coaches want their players to succeed. If I have you coach me, you are going to talk to the next person and tell them why they need to talk to me. Then I can walk into that next meeting and say I was told this is what you care about. I am making it frictionless across the process.

When interviewing for a product role, Jacob suggests actively identifying which stakeholders you should meet next. You might mention wanting to talk to the head of engineering, the VP of marketing, or the VP of sales. By suggesting these names, you insert yourself into the interview cycle rather than waiting for the company to lead. This makes it easier for the hiring team to know who to introduce you to. It also builds scarcity around your time. If you mention you are only available at specific times, you make yourself stickier in the organization and gain more knowledge about what the team needs.

I'm building scarcity about my time. I'm making myself stickier in the organization. I'm getting more knowledge about what people need. This is similar to selling an enterprise deal. You're building champions in the organization that love you and they're all coaching you on how to work with each other.

This approach helps create the leverage needed to negotiate a significantly higher salary. It is a process that works for both individual contributors and leadership roles. Jacob notes that even high-level IC roles, such as growth product managers at Meta, can be rewarded extremely well if the candidate takes ownership of the conversation. The goal of taking ownership is not to steamroll the interviewer. Instead, it is about being assertive and reading the room. You cannot control the mood or motivations of the person across the table, but you can control how you show up and navigate the dialogue.

I want you to take ownership because I can't control who you're going to get on the other side of the line. I can't control the mood they're in. I can't control their motivations. As a coach, I can't control how they show up. But you can control how you show up and we can work to navigate.

Jacob explains that successful negotiation starts with asking questions that force a company to state their values early on. If you are applying for an individual contributor role, you might ask how that position is valued compared to a management role. This sets a standard. When the offer arrives, you can use objective data to hold the company to their word. If the salary is lower than expected, you can point out the discrepancy between their stated values and the actual numbers. This shifts the conversation from logic to accountability.

Negotiation is inherently unbalanced because of information asymmetry. A large company negotiates thousands of times every single day. Most professionals only negotiate a handful of times in their entire career. The company knows the budgets and what every other employee makes. You are at a disadvantage from the start.

The game of werewolves shows the power of information. Even when outnumbered, a small group that knows the truth will win sixty to seventy percent of the time. Companies have significant leverage over you. They know what people make. They know their budgets. They know how to change those budgets.

Jacob notes that even executives often feel hesitant to push back on compensation. This is ironic because executives are the ones who understand how profit and loss statements work. They are often the ones who make the rules in the first place. These corporate structures are not set in stone. They were built by humans and can be influenced by humans. If you understand the system, you should feel more confident trying to change your part of it.

Effective negotiation requires a specific mindset regarding your value. You should never be so certain of your worth that you would not accept more. It is often best to avoid discussing specific numbers until late in the process. However, if a number is introduced early, you must know how to respond without limiting your potential earnings.

You should never be so sure of your worth that you wouldn't accept more. Another important piece is to never split the difference. Just because somebody says you started at 100 and they say 200, they come in at 150. That is lazy.

Splitting the difference is a common mistake that often stems from a desire to be polite or reach a quick resolution. This approach can lead to significant financial loss. Jacob shares an example of a chief revenue officer who had negotiated a severance package based on his total target earnings of $700,000. When the final paperwork arrived, it only listed his base salary. This change would have cut his payout in half.

The executive initially considered suggesting a middle ground to settle the discrepancy. Instead, Jacob advised him to ask a simple question to clarify the intent behind the change. This allowed the other party to correct the error without a confrontation.

Simply ask: Was that a mistake? We had discussed on target earnings. That was intentional. Was that a mistake? He said, oh, yeah, it must have been. Let me just tell the attorneys to fix it.

By asking if the change was a mistake, the executive recovered his full severance. Trying to split the difference would have cost him nearly $90,000 in that moment. Little things like compromising too early can be very painful in the long run.

Negotiation requires patience because haste creates risk. Moving slowly allows more time to collect information and build a compelling case. Many executives rely too much on logic and credibility while ignoring the emotional side of communication. Jacob believes this happens because corporate environments often feel soulless. People frequently hide their authentic selves just to survive. However, tapping into emotions and motivations is often where deals are actually made.

The slower you go, the more opportunity you have to collect information so that you can build a compelling case.

Using tactical empathy helps you understand what drives the other person. One effective strategy involves giving someone a positive reputation to uphold. For instance, you might acknowledge a colleague's history of advocating for others before asking them to address a pay gap. This frames the request around their own values. Jacob also recommends using the phrase, "If you were in my shoes." This invites the other person to look at the situation from your perspective and offer advice on how to move forward when a deal stalls.

Negotiation should be a collaboration rather than a confrontation. In a video call, it is easy to feel like you are in an adversarial position because you are face to face. It is better to imagine you are in the same room whiteboarding a solution together. This shift in mindset helps break down barriers and encourages both parties to share information freely.

Instead of us arguing over something, we're whiteboarding a solution together. I want collaboration in that. That's how we break down walls and barriers.

Success often comes down to making the conversation about "we" instead of "me." When you approach a problem as a joint effort, you move away from conflict and toward a shared outcome.

When an executive leadership team has standardized pay and equity, pushing for a higher salary may not be the best move. In one instance, a Chief Marketing Officer was entering a company where every executive received the same base salary and equity package. Instead of asking for more money, Jacob Warwick suggested focusing on severance protections. By framing the request as a way to protect the entire leadership team after a recent round of layoffs, the candidate turned a personal negotiation into a company-wide benefit.

Wouldn't it make us look good to proactively give everyone on the executive leadership team six months to show that they're safe and committed to the company?

This strategy allowed the CEO to look like a hero for providing better security to his staff. It also helped the new executive build immediate rapport with her peers because she was responsible for their new protections. When direct compensation is capped, finding ways to use the company's existing policies can create a win for everyone involved.

Creativity can also solve stalls when two competing offers look identical. Jacob shares a story of a CEO who had two $2.4 million offers and could not decide between them. Since the cash compensation was maxed out, they negotiated for a specific company car. Because the vehicle met certain weight requirements, the company could write it off as a tax expense. This added significant value to the contract without breaking the established salary budget. While a luxury vehicle is an extreme example, it shows that unconventional solutions can break a deadlock.

Negotiations should happen in person or over video call rather than email. When you communicate digitally, you lose control over the context of the conversation. A person might read your email while stuck in traffic or after a frustrating meeting, and the message might not land correctly. On a video call, you can see if someone is visibly frustrated or tired. This allows you to pause and suggest rescheduling to a better time so you can both get the most out of the interaction.

If I hop into a video call and I can see that you're visibly frustrated, I'd say, 'Would you like to reschedule to a time that feels more comfortable for you?' That is a blessing. You couldn't do that over email.

If an offer is rescinded or a negotiation goes sideways, the best approach is to lead with honesty and integrity. Jacob Warwick shares an example of a candidate who lost an $800,000 contract because she followed a coach's advice to be overly aggressive. This style did not match her personality or the culture of the executive team she was joining. To fix the situation, she called the CEO and admitted she had followed bad advice that did not feel right to her. By being authentic and taking ownership of the mistake, she was able to rebuild the relationship.

She got that deal back on the table for her authenticity and transparency. When things go south, approach it with honesty and integrity. Say, 'I made a mistake.' Take ownership. Extreme ownership really helps here.

Taking ownership of a mistake can often restore trust and salvage a deal that seemed lost. It is better to admit you were acting in a way that felt unnatural than to let a cultural mismatch end a career opportunity.

Negotiation is not a one-size-fits-all process. It requires a deep understanding of the person across the table. Factors like professional background, geographic location, and cultural nuances all play a role in how a conversation should be approached. Whether someone is a marketing leader from New York or a product manager from Dubai, their unique experiences shape their challenges and expectations.

Everybody is different culturally. Male, female, every little nuance is important. There are different challenges that everybody has to overcome.

Jacob recalls a moment speaking to a large group of women leaders. One participant asked if she should simply negotiate for 84 percent of a salary, given the existing pay gap statistics. Jacob reframed the issue by asking the mothers in the room if they would ever give that same advice to their daughters. This shift in perspective highlights the importance of fighting back against power imbalances.

When one person has the audacity to raise the precedent for their compensation, they help those who come after them. Companies often rely on what they have paid in the past. By pushing for more, individuals can help raise the tide for everyone.

If companies want to rely on precedent, have the audacity to raise the precedent because the next people in line will do that.

Jacob Warwick shares a case where a professional was facing a hostile takeover from a private equity firm. Instead of fighting the firm directly, which is usually a losing battle, they looked for internal allies. The person had a long relationship with the CEO, but the CEO was initially hesitant to act because he feared for his own job. The strategy shifted when they aligned the reader's goals with the CEO's own security. They showed the CEO that setting a strong precedent for the reader's exit or retention would eventually protect the CEO too.

Whatever precedent you helped me deliver, you're going to get two to three times that. So we need to set this up right.

This alignment turned the CEO and CPO into advocates. This approach underscores that people often act out of self-interest rather than pure kindness. In a capitalist environment, you must demonstrate how helping you also serves their own motivations. Jacob also emphasizes that these negotiations are about more than just one person. When individuals have the guts to negotiate for better terms, they act as a rising tide that creates better opportunities for everyone who follows them.

Negotiation is not a linear process with a simple step-by-step guide. Too many variables exist, such as company type, role seniority, and personal background, making it impossible to follow a single path to higher compensation. Traditional advice often makes negotiation feel overly academic or intense. Frameworks like BATNA or metaphors about hostage situations can be intimidating and may distract from the actual conversation.

Negotiation comes off so complicated and so academic. You're in the moment trying to have a conversation and have empathy and listen. But then you're like, what's my zone of possible agreement? Those things are all very true, but it comes off intimidating. When we try to focus so much on frameworks, we stop listening.

The most important tools in a negotiation are curiosity and empathy. If a person reaches a block, it usually means they have not asked the right questions yet. Real power in these situations comes from information and timing. Jacob emphasizes that outcomes are not predetermined. He challenges people to think about their long-term goals on a much shorter timeline to see what is truly possible. For example, he might ask a client what their five-year plan would look like if it were completed in just one year.

Negotiation comes down to information and timing. That's what creates power. You should never be so sure about an outcome because then you start putting a ceiling on your life.

Negotiation often focuses on finances, but human emotions are frequently more important. In a major movie franchise, a conflict between a famous actor and a writer stalled production. The studio offered the writer an extra million dollars to return. The writer refused because the money was not enough to overlook the previous disrespect. Jacob suggested that the actor should offer a sincere apology instead. Humility succeeded where money failed.

We asked the actor to humble themselves and apologize. That is what moved the deal across the line. Actually coming in and apologizing for the behavior is what got the deal back together and the million dollars was saved.

Money has a different impact depending on your situation. For someone earning a low hourly wage, a small raise is magical because it might mean being able to afford gas for the first time. For someone earning millions, a 10% increase is not enough to make them work with someone they dislike. Jacob draws inspiration from his own past. Twelve years ago, he was homeless and struggling to pay for gas. He now uses his negotiation experience to help people create material changes that compound over time.

Negotiations in Hollywood operate on a completely different scale than in the tech world. Jacob notes that while tech workers might struggle to ask for $20,000 more, Hollywood deals can shift by millions in a matter of days. He recalls a deal where a production company initially offered $5 million to an A-list celebrity. After an aggressive counteroffer of $22 million, they settled at $13 million within just two days. The discrepancy between a million and a billion is also massive. A million seconds is about 11 days, while a billion seconds is over 31 years. These scales show that you must change how you negotiate as you move into different rooms.

In Hollywood, we did this deal with an A-list celebrity. The company said, we want to pay her $5 million for this movie. The attorney came back and said we want $22 million. They went from $5 million to $13 million in two days. They are moving $4 million chunks at a time. We are over here in tech wondering if we can get $10,000.

To increase compensation, it is necessary to anchor high. Jacob points to research suggesting that individuals who anchor with an aggressively high number perform 75 percent better than those who aim to be reasonable. If you hope for $50,000 more, you might only get $15,000. However, if you ask for $150,000 more, you might end up with $70,000. If you have already committed to a range, you can explain that the scope of the role seems to have increased and ask to revisit the structure.

When receiving an offer from a recruiter, Jacob suggests asking if there is room to bump the number. If the conversation hits a wall, reach out directly to the hiring manager. Briefly mention that there is a sticking point and ask if they are open to a quick chat. Keeping communication short and confident is more effective than providing a long list of justifications. Confidence is often reflected in brevity.

The more confident you get, the shorter your communication gets. Sometimes it can be as simple as texting the hiring manager saying, open to chat. You do not give them any reason. It is just open to chat and then you control the conversation from there.

Jacob is on a mission to make the lessons he learned from successful people more accessible. High hourly fees can make expertise feel unobtainable, so he chooses to share his knowledge freely through courses and writing rather than gatekeeping it. This drive to help others stems from his own background. Growing up in an environment shaped by substance abuse and trauma, Jacob often felt powerless and unsafe. This early experience profoundly shaped how he views professional environments today.

I started to understand psychology a little bit differently because the same fear I'd have as a child, I could see in the boardroom. I could see the same fight or flight mechanisms, but that was far less scary. It is just money. Nobody is going to get hurt here.

By observing body language and recognizing when someone is in a tense moment, Jacob tries to help them feel safe. He spent his career obsessing over how to solve these feelings of fear, first for himself and then for others. Helping people navigate these high-stakes moments and witnessing their growth has become his most fulfilling work.

Taking a chance on yourself is a vital step in personal growth. For parents, this risk is about becoming the best version of yourself and showing your children that you can survive any challenge. Most of the professional risks involved are manageable and will not take away your home. Instead, they are opportunities to improve the lives of those around you. When you have more resources, you can be more generous with others.

If your cup overfloweth, you will be able to give more to others. It is not about whether you are worth it. If you are a generous person naturally, you can be more generous if you have more wealth.

Jacob shares that he used to have a negative view of wealth. He did not trust people with money and assumed they were unethical. He eventually realized that fearing wealth and not understanding it prevents you from having the chance to change things for the better. It is important to have the confidence to try new things. Even if you fail, you are failing forward and learning. You do not need to copy anyone else's style. You just need to find the approach that works best for you and makes you feel comfortable.

AI is a common topic in most modern discussions. Avoiding it can be a sign of a unique dialogue. Jacob jokes that he stays away from the subject because he does not want to be replaced. He also shares a philosophy about the role of a guest in an interview.

If you get the podcast host speechless, you're doing your job.

A successful guest provides enough unique insight to leave the host without a ready response. This impact shows that the discussion is moving beyond expected territory. It is a sign that the guest is offering a truly fresh perspective.

Negotiation does not have to be a complex corporate exercise. Simple concepts are often the most effective. Herb Cohen's book, You Can Negotiate Anything, is a helpful resource. It frames negotiation through everyday items like dishwashers rather than high-stakes tech acquisitions. This makes the fundamental concepts of exchange easy to grasp. John Lowry's Negotiation Made Simple also provides a clear and usable framework for these skills.

The concept of negotiation is really spelled out simple. It is not like going to market with Meta versus Instagram and the acquisition. It is like, here is an apple and here is an orange.

Robert Cialdini's Influence is another foundational text for understanding persuasion. Additionally, Radical Candor by Kim Scott is an essential tool for professional growth. Jacob credits this book with providing the confidence needed to be assertive in the workplace. Learning to be direct and honest can significantly elevate a career path. It provides a structure for communication that many people find difficult to master without a guide.

A personal rule for growth is to focus more on production than consumption. Jacob aims to create ten times more content than he consumes. This approach prioritizes active participation and sharing ideas over passive intake. It ensures that the focus remains on personal output and contribution.

Jacob finds value in low-stimulation media like the French cartoon Minuscule. With the constant noise of raising a toddler and a newborn, choosing mellow content provides a necessary break. This quiet time allows the mind to wander and find a bit of boredom. This is often where creativity begins. Constant high-energy children's shows can be overwhelming and make it difficult to think clearly.

Finding a little boredom and creativity. That's how you get creative. If it's constantly like Cocomelon and Paw Patrol and you can hear the beats in your head, you can't do that.

Jacob also relies on specific products for his daily routine. He uses Claude and Gemini as AI assistants. For his health, he uses MacroFactor for tracking nutrition and a Whoop strap for monitoring his physical stats. By paying close attention to his data and focusing on his sleep, he lost nearly fifty pounds in a single year.

A guiding principle for both work and life is to always give more than you expect to receive. This approach acts like an enhanced version of the golden rule. It is particularly effective in networking. Instead of trying to take something from a connection, you should focus on how you can help them. This mindset shifts the interaction from a transaction to a genuine relationship.

Always give more than you expect to receive. It is like a golden rule plus. That is how networking works. You do not network with someone trying to take. You say, "How can I help you?"

Jacob notes that this concept aligns with principles found in influential books on human behavior and influence. While these strategies are well-documented, the practice should stem from a genuine desire to add value rather than a calculated tactic.

Jacob Warwick serves on the board of the Cody Dieruf Foundation in Bozeman, Montana. This organization helps families in rural areas get access to essential healthcare. Jacob became involved because his son has cystic fibrosis. This genetic condition used to have a very low life expectancy, but medical advancements are changing that. One mother the foundation helped had three sons with the disease. She lost her first son at age 29 because she could not afford a lung transplant and did not know the foundation existed. When her second son needed the same surgery, the foundation funded a flight to Denver Children's Hospital and saved his life.

We funded the life flight to Denver Children's Hospital to get that life saving surgery and saved her son's life. The part that got me was that now the mama feels all this guilt because she could have saved her son's life if she knew we existed.

When Jacob's own son was diagnosed, he used his professional network to find support. Within 24 hours, he received calls from chief medical officers and the FDA. He learned about new medications that are lowering the age requirements for treatment. These medical breakthroughs are moving the life expectancy for those with cystic fibrosis from early childhood to age 70. Many children may never even experience symptoms because of these changes.