Tim Dempsey


Communication as a Culture

One of the reasons that I found myself working in venture capital is that I’m fascinated by business.

In VC, I get high frequency exposure to how different CEOs run their businesses and armed with countless deep-dives into the kishkes of venture-backed companies, it’s very clear that super-high growth can only be achieved when the CEO has great communication skills.

That’s ‘great’, not ‘good’, and it’s very hard to come by. 
The difference is often a lot more subtle than you may think.

“If a CEO doesn’t appreciate that their role is 90% communication, then they’re not a CEO worth investing in for the long term”
Credit: strategyzer.com

So, messaging is everything. “You don’t buy a yacht, you buy a dream” etc.
That’s CEO communication 101. You can’t recruit a team, raise a round or sell very much product without some skill in messaging.

But great messaging often masks bad/average communication, and great communication is critical to hiring, managing and keeping a team together.

Let me give a couple of examples:

Keeping your team focussed: let them know where they stand, always

We’ve all sent emails to people that highlight issues of asymmetric importance — whether that’s negotiating a fee, a pay rise, time off etc. — they mean a lot to you, but it’s just another thing for the CEO.

Scenario 1: You scrutinise every interaction over the next 24 hours wondering whether they have read the email, what they thought, why they looked up at you from their desk like that — you’ve put yourself out on a limb and that’s colouring your mindset right now. That’s a really frustrating place to be, as an employee, partner or advisor.

Suppose you don’t hear anything for a couple of days. Your work in the meantime is well below par because your mind is elsewhere, not just at work by when you’re at home with your family. The CEO must have read it by now — why aren’t they saying anything?

Scenario 2: CEO receives email and immediately QUICK REPLIES to say

“Hey, I’m super busy putting board papers together until Wednesday. But on first glance I can’t see this being an issue. I’ll reply more fully by Thursday AM”

or, if there’s a problem

“…I’m not sure this is going to be straightforward, but I’m confident we can sort something we’re both happy with. I know this is important to you, but I’m stacked until Thursday — let’s sit down then.”

There’s a huge difference between the two scenarios, both on a personal and professional level. Not only does it show a basic level of respect and care for someone’s personal concerns, but it helps them manage their mindset and re-focus on their day job, when they can trust that the CEO knows there’s an issue and is on the way to dealing with it,

That’s great communication — and it’s helping everyone, right? 
You can apply it to umpteen situations with the same compound effect.

Keeping your team engaged: don’t act unilaterally

Every start-up has big decisions to make on a regular basis, whether it’s about product development, marketing or HR — these are challenges , but also opportunities to make a team feel valued and respected.

I’ve been in situations where from one day to the next a CEO has declared that he’s leading a significant change in the company direction, and the first that the rest of the team hears about it is after his decision has been made — and presented as irrevocable.

A few reasons why this ‘visionary’ CEO is a dufus:

  • No one shares ownership for this plan — they’re just following orders. Consequentially, there’s less creativity, more pressure on the CEO to motivate the team, to ensure delivery and it’s an uphill struggle to do that against everything else a CEO needs to be mindful of (investors, partners, metrics etc).
  • Presumably people were hired for their skills and talents — they do certain things better than the CEO, and understand their domains more intricately — by not consulting them, the decision isn’t only likely to be a bad one, but its ramifications on their own sense of value (lack-of) in the organisation will be huge.
  • Unilateral decision making in a small team is disastrous for trust. No one knows when or how things will change next — it’s now a ship that can change destination at any point. There are better places to work. People will find them.
  • It’s impossible to make big decisions without spending some time thinking them over. So it’s either a hashed-decision or the CEO couldn’t be bothered to communicate during their thought process.

What does a great communicator do when he has to move with time pressures? Takes people aside, quickly canvas their opinion and instinct, works for a short time on a plan, shares it, involved them in a test and then implements it based on the results.

Everyone gets a turn on the conch. No megaphones allowed.

Great communication. No shocks, no crisis of trust, no valley of death.

Communication doesn’t need to be a super-power, just a priority

My point is that good communication isn’t a talent, it’s a skill that can be learned, developed and constantly refined.

It’s not about turning round afterwards with a full and frank “I fucked up” apology, openly listing your errors. As a start-up CEO if you find yourself in that position then you’ve already failed your team and investors.

Ahead of anything else, I want to invest in a great communicators. It doesn’t matter if your LTV:CPA ratio is through the roof or your growth rate is 50% MoM — if a CEO doesn’t appreciate that their role is 90% communication, then they’re not a CEO worth investing in for the long term.

So forget about manufacturing a company culture laden with mini-golf courses around the office and smoothies on-demand — you’re just outsourcing something that’s going to catch up with you.

The best ‘culture’ your company can have is one that encourages good communication on all levels. The earlier that a CEO prioritises that and really starts to live it, the better their company is going to perform. 
Hands down.

Radical Candor

I read Kim Scott’s book on Radical Candor a few weeks ago. It’s a good read. Probably longer than it should be, but it shows how candid communication makes building a company (amongst other things) so much easier.


One of the caveats is that being uber-candid doesn’t just mean barking out blunt feedback — it needs to come alongside radical empathy and care. You need to care about people before you throw them some home truths, otherwise you’re just being offensive.

It’s definitely worth trying this out, whatever position you play.

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