How to Talk the Talk at your Startup


Navigating the politics of a startup can be tenuous. Add in the fact that you’re a small startup of 6 people, and a dash of rocket-fuel from being in Techstars. Now you’ve brewed up a stew full of crucial moments.  And what inevitably arises from crucial moments are crucial conversations.

I’ve found the skills to have these crucial conversations invaluable. Especially when in charge of a company’s growth.

I’ve read countless books and articles that emphasize how a growth hacker must have close ties in marketing, product, and engineering. However, this task is difficult to put in practice. Having a very technical product only works to make this chasm greater.

We currently have four distinct visions for Tutum. They come from our CEO Borja, CTO Fernando, Biz Dev Graham, and me. We each have a very specific focus, but want to accomplish the same thing: create an amazing product that our users love. And equally as important, an amazing product that we love.

Borja is focusing on how Tutum can raise money (because we can only eat ramen for so long!), hiring, and getting the best mentors possible. Fernando is focusing on making our product better and better through new features, performance and stability fixes. Graham is focusing on keeping Tutum running and grounding our ideas to the reality of the financial numbers. I’m focusing on how to grow Tutum as quickly as possible.

In the end, the company can only move in one direction at a time. It’s my job to make sure my vision is well represented. To ensure the company vision is aligned with growth.

Working with such different silos of the company requires a lot of diplomacy. This can quickly become a delicate balance, and results in crucial conversations.

So what exactly is a crucial conversation?

I’m referencing one of the best books I’ve ever read, Crucial Conversations Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.

What makes a conversation crucial as opposed to run of the mill?

First of all opinions vary. Imagine two people see the same promising future. But one wants to offer the service free, while the other wants to charge a premium.

Second, stakes are high. You need to raise $1 million for your seed round, and you’re in discussion with a multitude of investors.

Third, emotions run strong. This startup is your baby, and there’s 50 other people telling you how to raise them.


So what makes me qualified to talk about having crucial conversations? While I’m not a verbal ninja, I’ve cultivated a self-awareness in how I interact with others. I may still completely fail in the middle of a crucial conversation. But I try to look back, analyze, and figure out how that conversation could have gone better. And if I have another chance at a re-do, I’ll try again taking a different approach.

I’ve also spent over 2 years as a professional firefighter/EMT. I’ve been on over a thousand emergency medical and fire calls. Every emergency call turns into a crucial conversation. I usually meet people when they’re having the worst day of their life. And more often than not this will involve opinions that vary, stakes that are high (life and death at times), or emotions running very strong. And more often than not, all three!

Here’s a picture of one of my last calls.


Lots of crucial conversations there.

So I’ve had some practice, but I can definitely get better. I view this as a lifelong skill to learn and improve.

I think it’s safe to say a lot of us, myself included, try to avoid crucial conversations as much as possible. They can be draining, weigh us down, and cause anxiety. We think if we ignore it long enough, it’ll just take care of itself. But this is rarely the case.

These conversations aren’t limited to the workplace either. Crucial conversations come up with family, friends, spouses, loved ones, and even your last text that you’re putting off replying to.

We really have three choices when faced with this situation:

  1. We can avoid them.
  2. We can face them and handle them poorly.
  3. We can face them and handle them well.

I realized that I was choosing options 1 and 2 almost exclusively before coming across this book. This kind of self-awareness sucked at first. I realized just how bad I was handling situations. But it made me eager to read on and figure out how I could start nudging myself to take on number 3.

Here’s some situations from the book which are potential crucial conversations:

  • ending a relationship
  • talking to a coworker who behaves offensively
  • asking a friend to repay a loan
  • giving the boss feedback about her behavior
  • critiquing a colleague’s work
  • talking to a team member who isn’t keeping commitments
  • asking a roommate to move out

So how can we start to have better conversations, and reach dialogue.

The first thing we need to do is fill the pool of shared meaning.

Each of us enters conversations with our own opinions, feelings, theories, and experiences about the topic at hand. This unique combination makes up our personal pool of meaning. We use this pool to inform every decision, and it powers our every action.

When entering a crucial conversation we both start with different pools of meaning. We have different opinions. We have different histories, experiences, and thoughts.

The goal is to have a collective pool of shared meaning. This means inviting people to share ideas even if they appear controversial, wrong, or at odds with their own beliefs. It’s important that everyone openly contributes to this shared pool.

I think two heads are better than one. And 6 heads are better than 2. Now when Tutum makes a choice it isn’t at the whim of just one person. Priorities, challenges, and cross-discipline understanding start to emerge in our discussions. Looking back, our choices almost seem inevitable when it comes from a pool of shared meaning.

We may start a discussion with twenty different things we want to accomplish in the next week. Everyone contributes and explains what they think will get us to our end goal. We’re now making product choices with growth in mind. We’re now making growth decisions with investors in mind. We’re now making investor choices with product in mind.

We make sure everyone on the team knows why we’re doing everything we’re doing. I think Borja does a great job of making sure there’s constant communication between all of us and that we’re all onboard with a shared vision.

There’s a very large difference in being forced to follow one vision, versus everyone contributing and rallying behind a unified vision.

The challenge will be to keep our vision aligned as we grow in size.

The Crucial Conversations book talks about their extensive study and research, where they identified the most influential people in their companies. They were surprised to find that the most influential people weren’t defined by their role in the company (you don’t have to be a C-level employee to have influence). Next, they followed these influential people throughout their day to find what made them different. They found that these people share 6 different mindsets/techniques.

  1. Start with heart
  2. Learn to look
  3. Make it safe
  4. Master my stories
  5. STATE my path
  6. Explore others’ paths

We’ll go through each of these concepts. I’ll give you something actionable that you can implement RIGHT NOW in your life. At the end you just might handle crucial conversations a little better. And with practice, like a champ.



Start with heart

Stay focused on what you really want. When we’re in the heat of the moment our adrenaline starts pumping. We lose our prefrontal cortex activity and we revert to our animalistic instincts (hint: this isn’t good for team building). In this moment people usually default to a win or lose mentality. You need to make a choice:

Do I want buy-in on a growth strategy, or win an argument

Remember that the only person you can directly control is yourself. Once you find yourself entering a crucial conversation you need to ask yourself:

  • What do I really want for myself?
  • What do I really want for others?
  • What do I really want for the relationship?

The last step, once you’ve figured all of this out is to ask:

”How would I behave if this were what I really wanted?”

After asking this question, I often find myself in a much more promotion-oriented mindset that actually cares about other people. And if I keep my cool, I can try and find out what we can accomplish together.


Learn to look

We each have our own “Style Under Stress.” When we come under stress we’re going to behave differently than our typical behavior. The two ends of the spectrum are silence and violence. Do you tend to raise your voice? or tend to fume silently? or maybe somewhere in between?

I usually go silent, purse my lips, and find myself waiting for the other person to finish, so I can tell them how it REALLY is. This is obviously counter-productive.

We have to learn to identify when we enter this cycle. We have to be on a constant lookout for when a conversation becomes crucial. And also identify when others move to silence or violence. Then we know we have to help bring them back to dialogue.



Make it safe

When we see others moving to silence or violence, we have to step out of the conversation and make it safe. After safety is restored, dialogue can continue. There’s two keys in making a conversation feel safe:

Mutual respect: Do others believe you respect them?

Mutual purpose: Do others believe you care about their goals in this conversation?

For example we may be discussing different strategies of referral codes, promo codes, marketing channels, amount of free trial, etc. But the mutual purpose we’ve created in our discussion was “acquire the most users with as little cost as possible.” Now we can brainstorm new strategies and evaluate old strategies based on this agreed upon purpose.


STATE my path

If you want to present your ideas to others you can either try and gain buy-in from them, or force your idea on them. Things will turn out much better if everyone embraces the idea. How do we do this? STATE. STATE stands for:

Share your facts

Tell your story

Ask for others’ paths

Talk tentatively

Encourage testing

Basically you want to start with the least controversial and most persuasive facts of your idea. Then work in how those facts relate and support your idea.

Ask the other person about their facts and how it relates to their story. State your story as a story – don’t try to disguise it as a fact. And finally, make it safe for others to express differing or opposing views.


Explore others’ paths


“Seek first to understand, then to be understood” –  Stephen Covey


In Stephen Covey’s book The 7 Habits of Highly Effective People, habit 5 is: “seek first to understand, then to be understood.”

Exploring others’ paths is about understanding the other person. People will be much more likely to understand you, if you show initiative in understanding them first.

You can do this by simply expressing interest in the other person’s views (“Hey Greg, I want to hear about how A & B will help user traction”).

Acknowledge the emotions people appear to be feeling (“you seem frustrated. Let’s back up, I want to understand where you’re coming from”).

Paraphrase and restate what you’ve heard to show that you understand (“So you’re saying A will reduce our monthly churn, and B will create a better onboarding experience for our users. Did I get that right?”).

And if they continue to hold back, take a best guess at what they might be thinking and feeling (“You haven’t said anything, but I think something’s bothering you. Do you think my suggestions of C and D are completely missing the mark?).

Once someone feels like you really care about what they think (one caveat: you actually have to care!) they open up and become much more receptive. Now you can actually have a productive conversation that turns into a win/win situation.

Hopefully you now have the tools to tackle your next crucial conversation. Whether it’s at home, in the office with your CEO, at a job interview, or trying to get out of a speeding ticket.

If you enjoyed reading about this topic, I’d highly highly recommend reading the book Crucial Conversations. It changed my life. It changed how I perceive all of my interactions with friends, family, coworkers, and strangers.

I’d love to hear from you! I want to hear how you handled a crucial conversation.

Or how you get buy-in from co-workers on an unpopular idea.

Any good ways to create and keep a tight-knit startup culture?

Thanks for reading!

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Posted in General, Growth, Startup
4 comments on “How to Talk the Talk at your Startup
  1. miueng says:

    “State your story as a story – don’t try to disguise it as a fact.” I wish more people would follow this advice, especially the politicians. Thanks for the book recommendation.

    • Bryan Lee says:

      Thanks for the comment! That’s also one of my favorite pieces of the book. Getting to realize that your opinion is exactly that, an opinion. People become much more receptive to you when you present your opinion as an opinion. And as a bonus it helps you stay open-minded and not become overly attached to your side of the story.

  2. H.L.Lee says:

    Enjoyed reading your perspective on communicating with co-workers. Here are some tidbits that I have learned from 30 years in the workplace, in no particular order:

    1. Really listen to the other person. Communication is two ways and each person should really listen to the other person for a constructive conversation to occur.
    2. Pick your battles – you can’t always expect to win the war and, in reality, sometimes, winning battles over the longterm can prove to be more victorious in the end.
    3. Prioritize – People can come to the table with many ideas but some may be more important than others. Prioritization brings focus.
    4. Don’t be afraid to make a decision, even if they turn out to be wrong ones. The more you make decisions the more comfortable and confidant you will be making them in the future…..and you WILL learn from your mistakes.
    5. Know yourself and your limitations – A good manager should be self-aware about what they know and don’t know; strengths and weaknesses.
    6. Have ground rules or an understanding about how final decisions will be made in the group – one decisionmaker (e.g., head of the group), by consensus, unanimous, etc.

    As you are learning, ofen the toughest challenges in life are dealing with all sorts of people!
    Thanks for sharing Bryan!
    H.L. Lee

    • Bryan Lee says:

      Thanks for sharing your experience as well! I will definitely be paying close attention to 4, 5, and 6. As I think those are the areas I have the least experience with but will be tackling much more often soon. Thank you!

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