How to find a mentor, and how to be one: Brad Feld on give first and telling stories instead of should

If you want to know how to find a mentor, or be a better one, the most useful thing in this conversation is a technique rather than a principle. When someone is about to make a mistake, do not tell them what they should do. Ask questions until you understand the situation, then tell them a story from your own experience.

Brad Feld is a partner and co-founder at Foundry, has been investing in early-stage startups for over 35 years, co-founded Techstars, helped shape the Boulder technology scene, and runs the Anchor Point Foundation with his wife Amy Batchelor. He has been writing candidly about entrepreneurship and mental health since 2004.

He is here to discuss his book Give First, his ninth.

What give first actually means

The phrase first appeared as a single paragraph in Feld's 2012 book Startup Communities, under the heading give before you get.

The point he was making: if you want a startup community to move, you have to be willing to put energy into it without defining what you get back.

And he was explicit even then that this is not altruism. You do expect to get something back. You just do not know when, from whom, over what period, or in what form.

His observation from Boulder, having started acting on this around 2006 when Techstars began, is that once enough people are putting energy in, remarkable things start to happen.

Why it is not paying it forward

Feld treats paying it forward as a cousin rather than a synonym, and the distinction matters.

Paying it forward is transactional. Someone did something for me, therefore I need to pay it forward. It carries obligation and emotional weight.

Give first is non-transactional. You put energy into things not because someone did something for you and not because you owe anyone.

His second contrast is positive sum against zero sum, and his example is the best part of the episode.

Challenged that sport is inherently zero sum, because someone wins and someone loses, his answer is tennis over the last twenty years. Every match Federer, Nadal and Djokovic played had a winner and a loser. And the relationship between the three was positive sum. Each got better through competing with the others, and together they elevated the entire sport, which is dramatically more popular now than it was.

He extends it to Billie Jean King's era, when women's tennis was professional but heavily subordinate to the men's game, against a present where it is often the more exciting of the two, produced by the same dynamic of competitors lifting each other.

The third element is multi-turn. You are not having a single interaction, you are engaged over a long period. Which is where paying it forward often falls short, when someone considers the debt discharged by one act.

His caveat throughout: this is a philosophy rather than a set of rules. Not that you never have a transactional relationship, and not that genuine win-lose situations never occur.

Is it still transactional if you expect something back

Michael's challenge is fair: if you know something will come around eventually, does that not blur the line?

Feld's answer is that the transaction is not between the two people involved. It is with whatever system exists around it.

His example is the podcast itself. He is not getting anything financial out of it, and book sales would not cover the effort. His reasoning is that getting the message out will have some good effect somewhere, and helping with what Michael is building is additive.

His honest concession: of course it is blurry. A philosophy should be a little blurry.

And his argument for why extreme transactionalism costs you: if 99.9% of your engagement is transactional, you are missing a great many opportunities for experiences that are unexpected, that go in unanticipated directions, and that come back to you in ways you did not predict.

Why he dislikes pattern recognition

Feld interrupts a question to object to the phrase, and the objection is worth having.

He dislikes it because for many people it functions as shorthand for not thinking hard about a problem. The worst version being extrapolating from one experience to how everything in the world works.

His more careful version: people accumulate experiences within one domain, one set of people, or one geography. Categorizing that is useful input. Treating it as a substitute for critical thinking is a weakness.

The forum method

The technique underneath Feld's approach to mentorship comes from a forum group in his early twenties, part of the Young Entrepreneurs Organization: a confidential group of ten peers meeting monthly with a defined process.

Someone presents a problem they are struggling with. Everyone else asks questions, Socratically, gathering information. Crucially, you ask questions of the presenter rather than of each other.

And then, at the end, you give an example from your own experience that you think is relevant to the problem. Not a solution. Just something relevant.

His account of why this is powerful rests on what the alternative assumes. Telling someone they are about to drive off a cliff and here is what to do assumes you are right about the cliff, and right about the information they are weighing. His extension of the metaphor is a good one: perhaps they want to drive off the cliff, because they have a car that flies and you have not had that experience yet.

His observation about how founders receive advice is the practical part. Most have an allergic reaction to being told they should do something, and the inner reaction is usually stronger than the outer one.

So his framing is deliberate. He is not telling anyone what they should do. He is giving them his experience to learn from if they choose, and they are free to ignore him or conclude he is wrong, because he often is, and because he may not have the right frame of reference or all the information.

His definition of the job: as a mentor, all you can do is give someone more information to consider, with context around it, and elicit more information so the context you give can be better.

And when to just answer

Feld is careful not to make it a rule, and the story he tells against himself is the reason.

In a board meeting, a CEO presented a real problem. Feld asked questions, then told a story. He could read the room well enough to know it was not landing. Another board member took his example somewhere unrelated. He asked more questions and tried again with a better-calibrated story.

At which point the CEO, pacing at the front of the room, told him bluntly that he knew Feld knew the answer and to please just say it.

So Feld said it. He cannot remember whether he was right or whether it solved anything.

His conclusion: sometimes you should be directive, and sometimes the other person wants you to be. Particularly in a managerial context, where people often want the manager to make the call.

Which is where he draws the line. These constructs are less about being a better manager and more about engaging as a mentor or board member, someone who is not functionally responsible for executing or for the outcome.

Commitment requires that they define it

Feld learned this in his mid-twenties running a software company, and it is the sharpest management idea in the episode.

If you want someone committed to an outcome, they have to define the goal.

Telling someone this must be done this way by this date produces compliance. Having them tell you what they will get done, by when, produces commitment. And the difference shows up in work quality, in effort, and in whether they actually believe in the outcome.

As a manager you do not have to accept their definition at face value. You challenge it and go back and forth. But what gets defined has to remain under their purview.

His illustration is the shift from waterfall to agile software development. Under waterfall, someone wrote a specification of hundreds of pages, tossed it to the engineers, and told them to finish by Friday. Under agile, on a short repeating cadence, the team responsible for building sits down and decides what they will do and what fits in the timeframe.

The constraint became the timeframe. The content became the team's decision. And he thinks that is generally applicable across all management and leadership.

Coach, mentor, advisor, therapist

Feld's taxonomy is genuinely useful, because the four get conflated constantly.

A mentor. You do not pay them. They have no obligation to help you. The relationship is not necessarily confidential or continual, though it is more effective when it is both.

A coach. You pay them, so it is transactional, and they treat it as a job. Confidential and continual by design.

An advisor. Someone experienced you pay to help with something specific.

A therapist. Overlapping with coaching in structure, and a different set of activities, a different frame of reference, and a genuinely different skillset.

His position on coaching is unequivocal: every leader should have one. His analogy is that every serious athlete who can afford a coach has one, and he adds one back himself whenever he is training seriously for a longer running event, because it is valuable to have someone watching and observing who knows you and has their own experience to guide you.

Where emotional intelligence actually comes from

Michael's question is why the emotional side of leadership gets so much less attention than the tactical, and why he only started developing it with an executive coach.

Feld prefaces his answer by acknowledging that there are multiple ways to be an effective manager, including top-down command and control, and that there are certainly people who thrive in that environment. His bias is that it has never worked for him, and that you can build very effective organizations another way.

His answer on where to start: for a leader hungry to improve on this dimension, a coach is probably the most powerful tool, and a therapist is probably second.

His reasoning is the part worth keeping. So much of becoming effective at what gets called emotional intelligence, or the soft side of management, starts with knowing yourself better.

His framing: everybody is the hero of their own story. And you cannot really know your story without understanding yourself, what has made things successful along whatever your own path is, and what is getting in your way. A great many people go through life never knowing those things, because they never put the energy into understanding themselves.

A coach helps with some of it. The next level down involves things that are hard to talk about, hard to confront, and take a long time to work through.

His description of therapy is characteristically plain: fifty minutes a week where he pays someone who has to listen, and he can spend the whole time saying whatever he wants, or nothing at all.

Why he writes

Feld has written nine books, and is clear he has not written them to make money, which he notes anyone who has written a book knows is not the economic proposition.

He writes because the way he learns is by writing. He listens well and takes in a lot of input, and until he writes it down he does not solidify the idea.

Which makes the books, in his framing, a selfish act: working out on paper what he actually thinks about something.

The story behind this one is instructive for anyone stalled on something. He wrote a first draft three years earlier, got feedback from around twenty people, and concluded he had a lot of work to do. He did not feel like putting the energy in, so it went on a shelf, and he did not know whether he would finish it, because he had not worked the ideas out well enough to feel good about them.

A year before the recording he took it off the shelf and reread it purely to judge whether there was anything good there. His verdict was that there was, and that there was a lot of work to do. Six months later the ideas were clear enough that he was proud of them.

Meaning

Michael's read on the book is that it coalesces around Feld's search for meaning, and asks whether that is fair.

Feld's response is that after forty or fifty podcasts about this book, nobody had put it that way, and that it lands.

His reflection is worth the episode on its own. Humans have searched for meaning since there were humans, in the difficult moments and the good ones, in success and in failure. And working through this book was a search for meaning, reflecting on forty years of business and technology, looking for a through line consistent enough to codify.

Forty years in which, he is careful to say, there have been many successes and many failures, plenty of disappointments and broken relationships. His view of anyone who claims otherwise after forty years is unprintable and entirely fair.

And his advice to anyone building something, whether a piece of art, a product or a company: if the only reason you are doing it is money, that is fine and it will be harder. It is far better to be doing it because it solves a problem you have. His phrase for the best version: you were put on this planet to work on this problem right now. Maybe not for the rest of your life, but right now.

The 5 things I took away from this conversation

1. Ask questions, then tell a story, and never say should. Brad's forum method is a technique rather than a value. Questions first, so your example is calibrated to their actual situation. Then an experience, offered as information rather than instruction, which they are free to reject.

2. Let them define the goal or they will not be committed to it. Told what to do, people comply. Having stated what they will deliver, people commit. The waterfall to agile comparison makes it concrete: keep the timeframe as the constraint and let the team decide what fits inside it.

3. Positive sum works even where someone loses. The tennis example is the most persuasive version of this argument I have heard. Every individual match had a loser, and the rivalry made all three players better and made the whole sport bigger. That is available in business more often than people assume.

4. Coach, mentor, advisor, therapist are four different things. They get used interchangeably and they have different obligations, different payment structures and different skills. Knowing which one you need is most of the problem.

5. Sometimes just answer the question. Brad tells a story about himself failing twice with the story method until the CEO asked him to stop and say what he thought. Any technique applied regardless of what the other person is asking for stops being helpful.

FAQ

How do you find a mentor? Feld's framing suggests looking for people willing to engage without defining what they get back, which is the give first disposition. He distinguishes mentors from coaches: you do not pay a mentor and they have no obligation to help, though the most effective mentorship is both confidential and continual.

What is the give first philosophy? Putting energy into a relationship or community without defining in advance what you will get back, while still expecting to get something eventually, from someone, at some point. Feld distinguishes it from altruism, and from paying it forward, which he considers transactional and often single-turn.

How should a mentor give advice? Ask questions first, Socratically, to understand the situation properly. Then offer an example from your own experience that is relevant to the problem, rather than a solution. Feld notes that most founders react badly to being told what they should do, and that the advisor may simply be wrong.

What is the difference between a coach and a mentor? You pay a coach, which makes it transactional and gives them a professional obligation, and the relationship is confidential and continual by design. A mentor is unpaid and unobligated. Feld recommends every leader have a coach, comparing it to serious athletes.

How do you develop emotional intelligence as a leader? Feld's answer is that it starts with knowing yourself, and that a coach is the most powerful tool for that, with a therapist second. His view is that many people move through life without ever putting energy into understanding what makes them effective and what gets in their way.

Also mentioned

• Give First, Startup Communities, Venture Deals and Startup Boards, among Feld's nine books
• Foundry and Techstars, and the Boulder startup community
• Forum groups at the Young Entrepreneurs Organization, source of the questions-then-story method
• The waterfall to agile shift, as an argument about who defines commitments
• Federer, Nadal, Djokovic and Billie Jean King, the positive sum illustration
• The evening a company's second floor collapsed during the Christmas sales season

Listen to the full episode

Brad Feld on Between Two COO's

Between Two COO's is hosted by Michael Koenig. Subscribe on Apple Podcasts, Spotify, or wherever you listen.