Quit: Managing Your Sales Career with Annie Duke

Learn strategic decision-making techniques and cognitive biases to avoid when managing the twists and turns of your journey in sales.

WSJ best-selling author of Thinking in Bets, former poker pro, and strategic business advisor Annie Duke graced the Bravado community for a conversation about managing a career in sales, specifically as it pertains to quitting.

Duke masterfully weaves poker strategies, business acumen, and psychological principles with surprising examples to explore our cognitive biases, how to overcome them, and how to use this knowledge to make deliberate career decisions.

This article is adapted from Annie’s conversation in December 2021 with Bravado CEO Sahil Mansuri.

Setting the Scene with Grit

The concept of grit has been popularized in recent years by Angela Duckworth’s bestselling book of the same name. It has weaseled its way into corporate mindsets, motivational speeches, and success stories. But Duke says grit – a combination of perseverance, persistence, and passion applied to achieve longer-term goals – is not quite what you think.

Grit is incredibly important in finding success. To have succeeded at something, you must first stick to it. But make no mistake, sticking to things does not equate to success. What matters is that you’re sticking to the things that you ought to.

While on the surface it may seem that grit and quitting are opposing forces, they’re actually decisions that work hand-in-hand. Grit is knowing when to let something go in favor of sticking to what you should. Quitting is simply that process of shedding what no longer serves you.

When it comes to choosing your current role and curating your career journey, you need to remain keenly selective. Unlike other areas in our life, we can’t have a diversified portfolio of jobs at any given time, so you need to hedge strategic bets to free up capital in order to earn it back elsewhere. And when determining your goals, Duke encourages you to think of them as an expressions of the things you value, rather than a specified, preset endpoint.

So, how can we all get better making decisions about what we ought to be sticking to?

A Lesson from Psych 101

Managing a career requires thoughtfulness and intentionality. There will probably come a time when you reach a crossroads and need to make a decision on whether to stay with your company/role or move onto a new opportunity.

Sometimes you’ll know exactly what to do. Sometimes the answer won’t come so easily.

If it’s not coming so easily, you might be asking yourself questions like:

  • “Do I stay in this position to see a quicker promotion cycle since there are other people leaving?”
  • “If I stay when everyone else leaves, I can be the hero and save the company from sinking.”
  • “I hate to leave the company hanging.”

Even when the equity upside of leaving to join a winning culture and sell a better product is tremendously higher, these questions linger.


A couple of psychological principles may be at play (among other things), including:

Omission Bias

Omission bias is a predisposition to perceive the harmful outcomes of taking an action (commission) as worse than the negative outcomes that come with inaction (omission), even if the possible consequences are similar.

Loss Aversion

Omission bias is related to loss aversion, or the tendency to avoid losses over pursuing equivalent gains (i.e. why losing something feels way worse/more painful/scarier than gaining something similar).

These two concepts may rear their heads in the form of something like this: if someone is in a job they don’t like, they would probably still prefer staying at it rather than taking a new job that they might not like – even though the former is guaranteed and the latter is only a possibility.

If you’re thinking of switching jobs because you don’t like where you are but you’re still hesitant about making the jump, ask yourself what the chances are that your current role (or company) is going to look better in a year than it is today. Your answer might be pretty low…sometimes even a 0% chance. Be honest. Then ask yourself the same question about the other job opportunity. What’s the probability that it will be better than your current situation? Greater than 0?

It can feel like a safer bet to ‘fail’ in situation you know (i.e. stay), rather than switch and potentially fail (i.e. go). We tend to regret losses more when moving into something new because we view it as an active decision we made and that led to failure, rather than failing and viewing it more passively.

But another way to think of it is that not making a decision is an active decision to stay on the path that you’re on.

Cognitive Dissonance

A third possible blocker might have to do with identity. If you believe that ‘you are what you do’ and your identity is wrapped up with your work, it can be hard to quit. Doing so might feel like you’re abandoning or quitting on part of your personal identity. This ties into a commonly discussed psych principle called cognitive dissonance, which occurs when our past actions and beliefs do not align with current or future actions and beliefs. The internal conflict of contradictory information creates tension with our innate desire to be seen consistent, or feel consistent for yourself.

Kill Criteria

Armed with the knowledge of these biases and tendencies, it’s now time for you to create tactical steps.

Duke recommends creating ‘kill criteria,’ or key elements with designated actions attached. This kind of structure removes emotion and bias from your analysis, thus aiding a more strategic decision.

For example, if your current company hits certain benchmarks by a preset timeline (e.g. 3 months), you’ll stay. If not, you’ll go. Look for all the signals: improvement, stagnation, decline. Setting these benchmarks will help you see these signs more clearly while also pre-committing you to an action.

Think you can’t do it alone? Duke recommends finding someone who loves you but will pay no mind to your feelings.

It sounds odd, so let’s break down what that means: being nice to someone means not wanting to hurt their feelings. But being kind to someone is thinking about them as a whole person, including the trajectory of their life; you will tell them whatever hard truths they need to hear, even if it is unpleasant to be on the giving or receiving end of that advice. Make sure you have kind people in your life – the real ones who won’t sacrifice your potential success in the long run for your feelings in the moment. Do keep in mind, this type of honesty doesn’t always come naturally, so you might need to explicitly ask for it. It can be tough to hear, but it’ll be well worth it to have this kind of support throughout your professional journey.

Defying the Odds

When creating your kill criteria, it is also important to ask yourself the real questions:

  • What percentage of the team actually hits OTE?
  • What’s the median comp of the sales reps on the team?

Then ask yourself: What’s my expectancy next year? Be realistic and honest with yourself. It’s harder than it might seem. Don’t sell yourself short, but also don’t think that you can be the one person to defy the odds.

Use these data points to compare yourself against the average and figure out where you stand. Are you better than the average? By how much? Perhaps you hit 125% of your quota, but everyone else in your org did too. Data points without reference are useless.

Use this information as your weapon for whatever you need next: negotiating higher compensation for your current role, performance metrics to use on your brag sheet, determining if you should leave for a new opportunity, etc. If anything, this information is useful for understanding the health of your sales organization. If no one in the org is hitting their quota, perhaps it’s time to look for a new position.

Expected Value

If you are still skeptical about creating kill criteria because that will force you into action, at least do yourself the favor of figuring out the expected value of the path you’re on. Expected value is how much you expect to earn or benefit over the long run, not just in terms of money. When you choose to put resources (e.g. time, energy) into one path, you are actively choosing to not put resources into other paths.

Duke recommends determing base rates, i.e. how often something occurs in a situation, when calculating the expected value of your current role. This may mean factoring in elements that aren’t easily quantifiable, like certain things your toxic manager does. But it is important to factor everything in because, depending on what you value most, you can trade expected value in terms of earnings for a better company culture or manager.

Often times when we have our sights set on a particular path, we see things through a myopic lens. Do not mistake this for ‘focus.’ Tunnel vision shields us from other paths that might actually have a higher expected value, and though counterintuitive, it can mean losing sight of the actual worth of the path we’re currently.

Another cognitive bias to watch out for: the sunk cost fallacy. An example of how this might play out is wanting to stay at your current role because you’ve put a huge amount of resources into something – like spending years of your career, long nights, and emotional investment into your role – even if the benefits of leaving vastly outweigh the current costs.

This is why kill criteria can be so effective. It’s simple, but it removes this kind of bias in your planning and decision-making.

Every choice we make has a sacrifice, so make sure you understand what forces are guiding your decisions.

Open for business?

All the same principles discussed above apply to founders as well.

For those running failing ventures, the quandry of choosing to shut down vs. trying to stay afloat is enough to lose sleep at night.

Some founders may argue, “I owe it to my employees to keep going.” In reality, you as a founder and leader owe it to your employees to make sure they have the freedom and space to achieve their goals. This may mean closing shop and freeing them to open paths they might not have seen before.

Especially for founders who have put a tremendous amount of resources into creating and running the venture, shutting down may feel like you’re losing it all (hello, sunk cost fallacy!). Once you make that decision, there’s no possibility of making it back. Another psychological bias that strongly applies to this scenario: endowment. We have a tendency to think something is worth more if you own it. I mean, have you ever tried selling something on a marketplace and had to have your expectations checked?

The kill criteria yet again are an effective tool in this scenario. Whether it’s about letting an early employee go or choosing to shut down, kill criteria removes the emotion from decision-making, something that could be even harder for a founder who has poured their heart and soul into the startup.

In terms of dealing with struggling employees, Duke highlighted another way to view the situation: as an employer, you have a responsibility to each of your employees to do right by them. No matter how attached you are, you owe it to them to free them up to find another position where they will thrive.

Some employees may actually strive to do better with the feedback they receive from you, so when you start to think about letting someone go, sit down with them and set those benchmarks. Don’t wait until the end when it’s too late to have this conversation – it can be easy to put it off and get stuck.

Avoid this by outlining the specific performance changes you wish to see over a designated period of time. This allows the employee to have ownership over their own benchmarks and performance, and because the commitment has been made outside of that particular moment, it’s a better parting for everyone involved if they do not hit these goals and you need to let them go.

Follow the Pheremone Trail

At the end of the conversation, a member in the audience asked a great question that we hear over and over again: is it okay to take calls from recruiters when you’re genuinely happy with your current company and role?

What came next was not anything we expected.

Duke dove into a discussion about ants. Yes, the small leggy creatures that crawl around outside and if you’re unlucky, you’ll find all over the food in your kitchen.

When a colony of ants moves into a new environment, they’re all scattered about. But when one finds a great food source, a pheromone trail is laid all the way back to the nest so that everyone else can follow it to and fro to bring bits back to their home base.

After the food source is found and this process ensues, however, you will still see some stragglers not following the pheromone trail or carrying their weight back to the colony. Are they lost? Are they slacking? Why don’t they just follow their buddies to the guaranteed food source?

Don’t get it confused – these “stragglers” aren’t freeloading. These ants, which account for about 10% of the colony, are continuing to explore the territory in search of another food source. Instead of falling into the honey trap, they are proactively keeping the colony secure by exploring the environment and mapping out new sources.

So…how the hell does this relate to talking to recruiters, again?

Ah, that’s where Duke got us, too. Really, it’s just a simple metaphor: your life, home, co-dependents, dogs, etc. are the colony, better offers at other companies are new food sources, your current role is the guaranteed food source, and you (should be) the ‘straggler.’ Talking to recruiters is exploring the environment in search of other opportunities, not because you need to – you already have a great guaranteed source, afterall – but for the just in case scenarios that always run the risk of arising.

It’s possible to have a wonderful job in all aspects and still find an even better job. We also live in an era of history with huge uncertainties, and you never know what unexpected consequences events may have on your company or industry. Plus, shit happens. Management changes and company priorities shift. If, for whatever reason, you’re in a position that you need to leave your current job, make sure you have a place to land and the tools to help you do so.

Founders and business leaders know that it’s the same thing for running a business: you put 90% of your resources into continuing to run the elements that are most successful, and you reserve 10% of your resources for testing new ideas.

If you can’t get enough of this conversation, check out Duke’s newest book coming out in fall 2022: Quit: The Power of Knowing When to Walk Away.

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