Category

Startup CEO

Fighting Confirmation Bias

I was mentoring a first time founder the other day who asked me, “How do you know what advice to follow and what advice not to follow?” (For the record, it’s a little ”meta” to answer that question!). I talked about looking for patterns and common themes in the advice from others and exercising judgment about how to pick and choose from competing pieces of advice. But then he asked me how I fight confirmation bias when I’m exercising judgment and incoming advice. Fighting confirmation bias is both incredibly important and incredibly difficult, and I’d never articulated my thoughts on that before, so I thought I’d do that here. The way you have to train yourself to fight confirmation bias…

Family vs. Team?

I used to describe our culture and our employees and our leaders at Return Path as a family. That was a mistake. It was just plain wrong. It served us well in some respects, but it bit us in the ass on others. Great groupings of people at work are teams, not families. You can have a highly functional family. But you don’t have high performing families. Work teams need to be high performing. Here’s what I mean. The family metaphor worked well at Return Path around the principles of caring for people and lifting each other up. Those elements of a culture are absolutely critical. I don’t regret them for a minute. But the downside of that metaphor is…

You’ve Seen One, You’ve Seen One

Like all CEOs and VCs, I’m a big believer in the power of pattern matching. I just wrote a whole blog post about the limits of pattern matching after hearing the quote above at a board meeting recently. But then a little alarm rang in the back of my head, and realized that I wrote about the value and limitations of pattern matching here years ago with an even better quote from my father-in-law: When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra. So rather that rewrite that entire post, I thought I’d just add onto it a bit here with a current example in my head about executive recruiting and…

Should CEOs wade into Politics, Part III (From Tim Porthouse)

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject. Your Leadership Game: “No Comment.” Should you speak up about news events/ politics? Most of the time,…

Everything vs. Anything

I heard two great lines recently applied to CEOs that are thought provoking when you look at them together: You have to care about everything more than anything and You can do anything you want but not everything you want Being a CEO means you are accountable for everything that happens in your organization. That’s why you have to care about everything. People. Product. Customers. Cash flow. Hiring. Firing. Board. Fundraising. Marketing. Sales. Etc. You can never afford not to care about something in your business, and even if there’s a particular item you’re more focused on at a given point in time, you can never get to a place where you care about any one particular thing more than…

Measure Twice, Cut Once

The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples: It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may…

You Don’t Need a CRO

One of the most common things early stage CEOs say to me once they find product-market fit and make a few sales is “I need a CRO.” The answer is almost always, “no, you don’t.” A couple years ago I wrote about the evolution of enterprise selling organizations in this post. Reading that is a good place to start this topic. Go ahead…I’ll still be here when you come back. Welcome back! So in the early days of a company, it’s all “selling on whiteboard.” The need that early stage CEOs have that prompts them to tell me they need a CRO is simple the need to have help selling. What the CEO really needs is a couple of very…

Chief People Officer Pitfall for Later Stage CEOs

(This is a bonus quick 5th post, inspired by long time StartupCEO.com reader Daniel Clough, to the series that ended last week about Scaling CPO’s- the other posts are: When to Hire your First Chief People Officer, What does Great Look like in a Chief Privacy Officer, Signs your Chief Privacy Officer isn’t Scaling, and How I Engage With The Chief People Officer.) As I’ve noted over the years, the Chief People Officer role is a tough one to get right and a tough one to scale with the organization if what you’re really looking for is a strategic business partner who can lead not just the important blocking and tackling in HR but innovates the people part of your…

Scaling Tip: Spend Less Time Talking. And Spend More Time Talking

One of my top 10 scaling tips for CEOs as they take a business from startup to scaleup keys in on communication patterns. As your company grows from 0-25 employees to a place where you no longer work hands-on with most of the team, which is really >25 but gets more and more true at every step beyond that, you need to rethink how you handle employee conversations in many ways. My tip sounds confusing, but let me break it down. Spend less time talking. The less you know about the day to day details of everyone’s job and experience, the more time you need to spend learning and keeping in touch with those details from others. The only way…

Onboarding Executives

I wrote a colorfully-named post years ago called Onboarding vs. Waterboarding, which detailed out some of the general principles around onboarding new employees that our companies have used over the years. A few weeks back, one of our clients and fellow CEOs of a Series C Ed:Tech company asked me for tips on onboarding senior executives, and some of what I said varied from or built on that earlier post. Here are a few of the themes we riffed on: Special thanks to my friend Amir for inspiring this post!

Should CEOs Wade Into Politics, Part II

I’m fascinated with this topic and how it’s evolving in society. In Part I, a couple years ago now, I changed my long-held point of view from “CEOs should only wade into politics when there’s a direct impact on their business” (things like taxes and specific regulations, legal immigration) — to believing that CEOs can/should wade into politics when there’s an indirect impact on business. In that post, I defined my new line/scope as being one that includes the health and functioning of our democracy, which you can tie to business interests in so many ways, not the least of which this week is the Fitch downgrade of the US credit rating over governance concerns. Other CEOs will have other…