Note To Startup Founders: Communicating Leadership and Easing The Sting Of Surprise

By April 3, 2015February 3rd, 2019No Comments
J. Kelly Hoey - Build Your Dream Network

A split. A pivot. And a fold.

Not poker, simply three of the startup conversations that have landed in my inbox over an equal number of weeks. I’ve previously posted about the importance of regular communication with investors and key stakeholder communities. These recent startup turns, for the worse or better (depending on your perspective) provide an opportunity for me to step back on that soapbox.

Being a startup founder, by definition, means you are facing uncertainty and taking on unexpected challenges. Regularly communications with key stakeholders during your disintegrating or troubling startup times eases the sting of surprise (plus disappointment) when the only thing that turns out to be disruptive about your startup is its founding team dynamic or hiring practices or product focus. Difficult conversations during those dark days may be the hardest thing you as a founder undertake — not because you’re stressed, or running out of money or lacking hours in the day — rather, those conversations are hard because they require facing up to your role in creating a situation which isn’t going as well as initially laid out in your polished investor pitchdeck.

No one likes delivering less than positive news — especially when the possibility stakes are high. I have to agree, facing a bad situation by putting your head in the proverbial sand of being too busy executing seems a lot easier than owning up to your execution warts and founder flaws.

But here’s the rub: investors and stakeholders invest in founders. Owning up to your role when something is not going well with your startup venture says more about your strength of leadership (and why we invested in you) than the ‘all is swell plus here’s what I need from you’ founder communication. Communicating in the dark days doesn’t set off the doubting-the-startup-CEO alarm bells, on the contrary, silence followed by an awkward “hey, here’s why you haven’t heard from me in a while” email does.

Don’t lead yourself to further startup woes by a communication failure.

If you’re a founder by definition you’re visionary and determined — that’s why we invested in you. You’re also imperfect and facing business challenges head-on for the first time — what better alignment of the new business venture stars for something to go completely, fabulously, wonderfully wrong? Your startup troubles? Not a big [insert F-Bomb] surprise! Investors have either seen it, lived it or anticipated it. When we invest at the early stage, we’re not just giving you our money, we’re also tossing in our experience and trust.

In the turmoil, you need to lean in to the experience of your investors.

In the uncertainty, keep talking.

And remember, it’s always easier to recover an investment than it is to recover trust.

J. Kelly Hoey

J. Kelly Hoey

Kelly Hoey is the author of Build Your Dream Network (January 2017 / Tarcher Perigee). She has been lauded from Forbes (“1 of 5 Women Changing the World of VC/Entrepreneurship”) to Fast Company (“1 of the 25 Smartest Women On Twitter”) to Business Insider (“1 of the 100 Most Influential Tech Women On Twitter”) and Inc. (1 of “10 Most Well-Connected People in New York City's Startup Scene”). Empowering A Billion Women By 2020 included her on their list of the “100 Most Influential Global Leaders Empowering Women Worldwide”. Not bad for a former corporate lawyer. She’s a limited partner in two emerging tech funds (Laconia Capital Group and Lattice Ventures) and can frequently be found on Twitter @jkhoey.