Be Authentic When Someone Asks How Your Startup is Going

by Scott - 4 Comments

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So how is (enter startup name) going?

Effective conversation

Many people answer this question with some iteration of “good” regardless of where things stand. I’ve talked with founders who I know are flailing, yet they still come up with some anecdote that things are “going well”. I’m not surprised at this behavior; we live in a world that says show your best and hide the rest. I just think it’s an ineffective, unsustainable paradigm. So save the dog and pony show.

When people ask “how things are going,” it’s far more productive to be honest and authentic. I have far greater respect for and more meaningful interactions with people that are. 

Why You Should Always Be Authentic:

No one is perfect. Everyone just pretends to be to protect their carefully constructed company/self image. When you’re authentic with someone you’re taking a risk. Others acknowledge and appreciate this courage. They also empathize with your humanity. Thus, a more powerful connection is forged because they can relate to the struggles and vulnerabilities they’ve often gone through themselves.


You’ll never receive help from someone if they don’t know how they can help you. This is why it’s far more effective to just be truthful about challenges if they exist. I will happily try to help out pretty much anyone I meet, but you need to tell me how I can help you first. This means letting me know if you’re struggling and what your current challenges are.


Most people rarely give the real deal in situations that call for it. That is why those that have the courage and humility to do so stand out. If I’m completely honest, I find myself putting a greater effort into helping the people I meet that stand out. Why? Well for starters they’re were engaged enough in our interaction to tell the truth.

Rules of thumb

Within the context of honesty and authenticity there are definitely some caveats. Complete and overt honesty is not entirely appropriate for every situation. It’s most effectively used when you have developed at least some level of rapport with the person you’re interacting with. The overtness of you’re honesty should be calibrated with the level of rapport you have with that person.  The first time I meet you avoid telling me how your whole world is crumbling down. It’s just awkward. You need to frame it differently. One way is to just say you’re going through some adversity. I respect when someone acknowledges this. It takes courage and is the sign of a leader. Leaders show their scars.

When you’re openly honest, exercise humbleness, awareness, and social finesse. What do I mean? If things are going incredibly well don’t be a braggadocios tool. You can humbly convey the same message by simply saying that all your hard work is finally paying off. On the other end of the spectrum, don’t mope if things aren’t going your way. No one wants to hang out with or help mopers.

Who do you like better? Which is a more effective conversation?

A good way to tie all of this together is to juxtapose two responses to an interaction that occurs frequently in the startup eco-system.

Imagine there is a founder who you’ve spoken with 3 times at a few events. Unbeknownst  to you, he has been on the fundraising trail for 6 months with no success. Which is a more memorable interaction following the infamous “How’s [enter startup] going”

Response 1: “Its going. Just doing the whole fundraising thing. Going pretty well, but these VCs are tough! You know how it goes”

Response 2: “Honestly it’s been a challenging few months. I never imagined it would be this difficult getting funding especially because all anyone wants to talk about is how easy it is to get money right now. I’m not discouraged though. I’ve learned a ton and I feel like each interaction I’ve had gets me closer to receiving the funding we need to grow. At this point, I’d love to get insight from people who’ve done it before and actually know what they’re doing. Do you know anyone I should talk to?

The answer is obvious.

Always be authentic even when times are tough. You’ll gain greater respect, forge more meaningful relationships, and achieve your goals faster.

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