Mastering the art of board and investor communications

Surfboard team

Published on Oct 17, 2023

Your relationship with your board and investors has the power to make or break your company. That's why Trevor Gary, founder and CEO of Micruity has established an impressive practice for communicating with his board and investors.

Listening to Trevor talk about his practices is like taking a masterclass on board and investor comms. And while you don’t have to approach things exactly the same way to see similar benefits, there’s a lot to be learned from his approach.

Here are four key lessons we learned from our conversation with Trevor:

Embrace candidness and transparency

It takes effort and intentionality to be open with your board and investors (even for Trevor, who admits overcommunicating is his second nature). But it doesn’t have to be a daunting, formal process.

The most important thing is to commit to a manageable cadence—whatever that looks like for you—and make sure you stick to it. If you send weekly updates, then weekly updates always go out.

Then take the pressure off yourself to make every update as thorough and detailed as possible. Some weeks you might send an update on a big marketing campaign or your current sales pipeline. Other weeks, you might literally just jot down your current thoughts, even if they aren’t directly related to the business. A lot of the time, your board and investors just want to get a sense of your headspace.

Side note: Trevor has set an impressively consistent update schedule. It looks like this:

Weekly short “blogs” on anything top of mind

Monthly financial updates, including projections, revenue, and runway

Quarterly deep financial dives

As a result, it’s pretty rare for a board member to ask a question in a meeting that wasn’t already covered asynchronously.

Get comfortable with negative updates

Nobody wants to share bad news with their board and investors, but at some point you’re going to have to. Navigating those moments successfully comes down to three things:

First, you have to accept that there’s almost no chance you didn’t have responsibility in what went wrong. It’s not just about identifying what went wrong, but really owning it. Mistakes and failures are an inevitable part of growing a business.

Next, you want to have some sort of plan in place before you announce the bad news. It doesn’t do anybody any good to share a negative update with no context. Your plan doesn’t have to be comprehensive, but you do need to say something about how you plan to correct the situation (and prevent a similar situation in the future).

Finally, quantify it. What is the specific, concrete impact going to look like? For example, if you need to shift money out of next year’s budget to make up the difference, how much? This can feel scary (it’s rarely deathly scary, according to Trevor) but giving concrete numbers helps everyone understand exactly what’s happening.

As you follow this process over time, you’ll start to notice that the highs feel less high, but the lows feel less low, too.

Spread accountability out

Regular communication helps you establish confidence and trust in your relationship with your board. But beyond that, transparent communication is a great way to spread accountability out. If something goes awry, everyone who was involved in or aware of the decision has shared responsibility—it isn’t just on you. And there’s comfort in knowing that if anyone had seen something bad coming, they would have suggested a change of course.

Make time to build relationships

As a CEO, cultivating relationships is one of your single biggest jobs. The relationships you build with your board and investors are vital to the success of your business, and you need to make time to work on them. It’s as important as closing deals, designing an HR program, and building scalable solutions.

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