Mentors 4/18: Be Direct. Tell The Truth, However Hard

Today’s installment of the Techstars Mentor Manifesto is #4: Be Direct. Tell The Truth, However Hard.

Let’s start with “Be Direct.”

At some intellectual level, being direct is easy. You just say what is on your mind. You say it in a declarative way. You lead with it and support it with either experience or examples.

But humans have a very difficult time being direct. Many of us can’t get to the point. We thrive on inductive reasoning. We are passive aggressive in our behavior. This is especially the case when we don’t know the answer to something or when we are uncomfortable with the truth.

Reflect for a moment on how you answer a question when you don’t know the answer. Do you use the magic and wonderful phrase “I don’t know.” Or do you skirt around the question, searching for an answer that is somewhat relevant, while reframing the question more to your liking. Or do you just spew out whatever comes to mind, extrapolating truth from one data point you have lurking in your brain somewhere?

Don’t do this.  If you don’t know, say you don’t know. But if you know, be direct.

You might think this contradicts Mentor Manifesto #1: Be Socratic. Remember that “be socratic” doesn’t just mean “ask questions”, it’s all about asking questions to get at the why of something. They key is that when you get at the why, and really get at it, then flip into being direct.

Now, consider the concept “Tell The Truth, However Hard.”

At 48, I’m no longer able, or willing, to lie. As a kid, I’d stretch the truth to exaggerate my own self-importance or the perceived excitement of a story. I did a few things I was ashamed of and lied to cover up and avoid exposing what I’d done. But whenever I got caught in a lie, which was most of the time, I felt badly about myself. My parents handled this really well. Rather than punishing me, they would talk about the deceit and make me face it. They were calm but direct and unyielding. At some point I realized dealing with the ramification of getting caught in a lie was much worse than telling the truth in the first place. I owe it to my parents for instilling this value in me.

By college I don’t think I lied very often. I still exaggerated the truth, but never purposefully lied. The next person to whack me over the head about this was my first business partner, Dave Jilk. At Feld Technologies, I was the primary salesman although Dave sold plenty of business over the years, especially with existing customers. I often made Dave frustrated with two behaviors. The first was when I oversold something and we ended up starting a new client relationship with expectations that were far out of line with what we could deliver. The other was when I was selling Dave on my position, trying to convince him of something by stretching the truth, exaggerating the wonderfulness of the outcome, or, in some cases, just trying to push through with the force of my personality, regardless of the reality of the situation. Dave would regularly challenge and push back on me, which eventually helped me realize that overselling, exaggerating, and overstating the situation ultimately lowered my credibility.

The killing blow for me on lying was when my first wife had a year long affair. The level of deceit in that dynamic, including between the two of us in our inability to be direct with each other about how we felt and what was going on, along with the corresponding emotional fallout for me, was overwhelming. I made an internal commitment to myself to never do that to someone else, regardless of the situation.

I proceeded to get involved in a relationship with a person I’d describe as a “truth teller” or a “fair witness” (for those of you who are fans of Stranger in a Strange Land.) Amy is incapable of not telling the truth, no matter how difficult, and after 23 years of being together, that has become deeply ingrained in my value system.

That doesn’t mean that I don’t make mistakes. I make a lot of them. All the time. And when I do, and I realize it, I own it. Which is another version of telling the truth. It’s easy, especially as a mentor, to gloss over the fact that you made a mistake. But it’s much more powerful to the mentee when you own your mistakes and correct them.

Linking together the ideas of “being direct” and “telling the truth” is very powerful. You end up holding yourself up to a high standard of behavior and communication. And you set an example for those you mentor, just like I learned from my parents, Dave, and Amy.

  • A few thoughts –

    Though I’ve been a truth-teller for years, I’m newly appreciating the value of honesty in those around me. You touch on this a bit w/ the story abt Dave calling you on the exaggerations, but I want to focus on that aspect.

    If you are constantly lying, ‘stretching the truth’ or whatever you call it – stop. The people around you will quickly sort out most of the lies, and from that part forward, will only only believe what they can verify in real-time (i.e. you say the sky is blue, I’m gonna look + confirm). Once this pattern is established in a relationship, one of two things will occur:

    – if the liar is someone I can walk away from, I do. Once the trust that comes from simply (+ consistently) telling the truth is gone, what’s left?

    – if the liar is *not* someone I can walk away from, then things get really complicated. I have to filter everything that is said + done against previous lies, known truths, etc to evaluate the current situation. (‘is this another lie? What did [person] say last time?’). It takes an incredibly high level of energy + commitment to maintain this.

    This is grade-school stuff, obv, but it’s worth remembering: if you’re lying, you’re broadcasting to the world that you can’t be trusted. And that’s something you can never buy, no matter how ‘wealthy’ you are. You have to earn it and I may not be willing to give it back to you.

    • Great distinction about “stretching the truth” being the same as lying. It seems to me that many people who want to be a “big” contribution (and I’ll include myself in this, particularly in my younger years) sometimes fall prey to the energy of the moment and become guilty of this sort of deception – of self and of others. The result is still a lie, though, and the faster it’s caught and cleaned up the better.

      I also wholeheartedly agree with the comment about how much energy it takes to maintain the relationships with liars we can’t walk away from. The small handful of these that I have left in my life are providing valuable (though not very enjoyable) long term lessons of what happens when I don’t pay enough attention to early warning signs that someone’s value system doesn’t match mine. I have succeeded in walking as far away from them as I can, and in future years I *will* be able to walk away completely. My goal now is to ensure that, until then, the toll it takes on me is as small as possible.

  • Joah Spearman

    The older I get the more I realize that truth is something that is best coupled with empathy. Ultimately, you have to seek to understand before you can be understood and part of telling the truth is knowing that you’ll never know someone else’s truth until you hear it directly from them rather than assuming you know what someone has experienced or what’s best for them.

    • Empathy is crucial. I’ll riff off this in my post today.

  • Great post! I tend to see lying tied to ego. Mentors, advisors and investors lie so their perceived “value” doesn’t decrease.

    It becomes an even bigger problem when an entrepreneur takes bad advice and makes unnecessary and unsubstantiated changes.

    As with your example when Dave challenged you, it’s very important to challenge any feedback, even if you agree with it.

    • You’re right, Steven. So much of it could be tied to ego, which is why I find it so important to check my ego at the door when it’s time to sit down with companies. You hit it on the head — it’s important to challenge not only the founder on their theories, but the feedback. Companies ask me how they ought to interpret feedback; my response is often that they ought to give careful attention to consistent feedback, and when they get an “outlier” in feedback, to flesh that out with their lead mentors. Because outlier feedback could be the winner, you never know, but all feedback ought to be fleshed out.

      • Thanks. You bring up a very interesting point that I didn’t associate until you mentioned consistency. Good interviewers know how to ask the same questions in different ways to ensure that the answers they are getting are consistent. Sounds like that would be a beneficial strategy for anyone getting feedback.

  • Great post, no lie. Empathy acts as the governor of telling the truth, especially when asked to give advice. If you have true empathy, empathy overrides all the motivations to lie.

  • Excellent.
    My only quibble is the world ‘declarative.’
    The problem I have with it is that this represents a style of communication that inhibits discussion. I am sure this is not what you meant but it is a word to be careful with.

    • Hmm. What’s a better word?

      • I’m not sure because I’m not clear quite what you meant by ‘declarative’ in this context.

  • Rick

    I think an honest analysis of the question asked my a mentee is important. Sometimes questions sound like they are open to partnering on the discovery of the answer. Hence the ‘thinking out loud’ offered by the mentor. Know if the question requires a direct answer or if the person asking the question is looking for any opinions they can use.
    One issue is mentors selling mentoring. When I mentor I try to ensure selling something to the mentee is never in the mix. If I find the mentee is stuck not able to get the help they need. Then I’ll offer services. Sometimes I see people selling instead of mentoring and that’s not good. It can confuse the mentee because they aren’t getting an transparent explanation.
    For example I’ve had mentees who needed software developed but could not find a vendor. I explained their project from their view and the view of a vendor. Then I provided a breakdown on what I would do if I was the vendor. It allowed them to *see* the profit centers of the project so that they could better understand how to deal with vendors.

  • Yes! It’s a given that mentors should be direct and not lie or stretch the truth about their feedback, but I think the same applies to the companies being mentored. If anything, they are likely to be the ones that are stretching facts and “faking it” a bit. But I think they should be straight with their mentors. It’s a big let down for the mentors to later find out that the startup they were mentoring was hiding something or didn’t tell it as it is. That’s serious, because it could invalidate the whole mentoring advice.

    • Rick


      • +2

        • +3

          • +7 (the new math)

          • Rick

            “the new math”
            That reminds me of the TV show Taxi. Where Jim comes to work one day and Louie (the boss) asked “Jim where have you been?” Jim says “I don’t work weekends boss.” Louie says “Jim you’ve been gone nine days.” Jim says “I thought we switched to the metric system.”

          • exactly

  • Great post. One of the great things about getting older is learning to see through your own bullshit. Oftentimes that only happens after something horrible (i.e. an affair by your partner). But if you can get past it an integrate it, there is a greater sense of freedom in life.

  • learned how to be ok with the answer “i don’t know” from my 4th grade teacher, Mrs. Perry… so invaluable

    it doesn’t always go over well with some people (a partner who wants a commitment, clients/investors who expect you to know everything), but you probably don’t want to be connected to someone who can’t handle the unknowns

  • Jonathan Fields

    Completely agree. Interesting challenge in the context of the mentor/mentee relationship is that, often times, the mentee “needs” honestly, but “wants” validation, on two levels. For both the person and the idea. Sometimes honestly leads to validation, but often, it doesn’t.

    When that happens, the mentee has to be able to parse data from emotion and idea from identity. That’s a tough task for any person on any given day. Even tougher when you’re in the altered, attached and, what our friend, Jerry Colonna calls “delusionally optimistic” state of starting a venture.

    Not that this in any way diminishes the need for honestly. If anything, it elevates it. But it also gives context to the potential response, what’s driving it and how to be honest in a way that cultivates receptivity over rejection.

  • Alex Wolf

    Having been raised by a very fair and direct person, lying was so frowned upon it never occurred to me. But further still, this piece should be paired with @JerryColonna’s recent Being Fierce piece and talk –

    • Jerry’s piece is dynamite.

  • I could not agree more. I have lived by this for long enough that my wife had a shirt made for me embroidered with “Will tell you your baby is ugly…” because startup entrepreneur has to learn that their baby really is ugly, and I will not hesitate to tell them (As constructively as I can!)

    • Great shirt, Troy. That’s a great analogy — these companies are really the children of the founders, and it’s hardest but most important to dig deep and share honest thoughts in a constructive manner.

  • Brad,

    Great post.

    This discussion raises an interesting dynamic for a mentor, which I’d like to do a bit of a deeper dive on, which is: don’t lie, even when your position is contrary to what a startup wants to hear.

    I recently experienced this when mentoring a team who was figuring out a go-to-market strategy, and their position didn’t make a whole lot of sense to me. They asked me my thoughts, and I told them they might want to consider a pivot and try x approach instead. I could tell immediately that me answer wasn’t what they wanted to hear.

    Part of being a mentor means being honest; it’s about helping the companies first, and giving them your true thoughts is more valuable then being a “yes person” and simply validating a position that the founder thinks to be correct. While it’s nice to make friends, it’s more important to be okay with taking a position that the founder may not want to hear. It’s about pushing them to think about their ideas, their strategy, and their execution. Worst case, this results in a spirited conversation that pushes both parties (mentor and founder) to flesh out the position and come up with a clearer understanding of the issues at play.

    There is also the element of knowing when a mentor ought to acknowledge that, despite certain advice to the contrary, a company has taken a position and run with it. When that happens, I find it’s better to then support the company in that decision, recognizing that a founder is the one calling the ball, and our role is to help them execute once they’ve dug in on a plan. Make your position known, come up with a thoughtful rationale, and if the founder doesn’t like it, it’s not a “pissing contest” at that point. We support our founders rather than allow there to ever be sour grapes about a founder not taking our honest advice.

    I might not always be right, but I will always be honest.

    • “It’s about pushing them to think about their ideas, their strategy, and their execution.”

      I’m fortunate to have some great mentors and friends, who do precisely that. Probing founders is the best thing a mentor can do. Taylor Davidson asked us one question, which ultimately pushed us over the edge to completely pivot our product earlier this year:

      • Bam! That’s awesome that you have such a great mentor in Taylor.

    • Totally agree. I would add that in addition to confidence, humility helps mentors and founders maintain an open dialogue.

  • Angus Shaw


    Great post, and the corollary is also worth mentioning:

    As an entrepreneur, I must be coachable. When I am presented with the truth, I must accept it, own it, adapt my life or my business to embrace it, no matter how hard. My mentor presented the truth in this unequivocal way because they see the impact these leadership behaviors or management decisions are having on me or my company and believe I am up to the task of making this change. When I’ve made the change, I will thank them for their insight, because it is the source of my success.

  • James Mitchell

    See Alex Kozinski’s (Chief Judge of the Ninth Circuit) in U.S. v. Alvarez:

  • James Mitchell

    Let’s assume you are firing someone because they just are not smart enough. Do you say, “You’re just not smart enough to work at Foundry Group” or do you come up with another approach, such as “We thought we were going to expand and we needed you, but it turns out not to be the case.” There’s nothing they can do about being stupid so telling them they are stupid provides no useful feedback and just hurts their feelings.

    • As I mentioned in the post “Brutal Honesty Delivered Kindly” – – firing a person is a challenging case.

      “I especially keyed in on Transparent, Authentic, and Empathetic as these three are core personal values of mine. However, these three ideas often come into conflict. It’s hard to be transparent and empathetic at the same time. Consider the situation where you fire a person. Legally, you likely have some constraints on what you say, limiting your transparency. You want to be empathetic to the person you fired, so this again limits your transparency (or, if you are transparent, you likely aren’t being very empathetic.) And then, at a meta-level, you will have some internal struggles with your authenticity around this situation.”

      Also, “being stupid” or “not being smart enough” is very subjective – I’d agree that it doesn’t deliver any useful information. Instead, I’d focus on the “why” of why they are being ineffective in their job.