Category

Human Resources

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…

Camera On, Mic On

At my last company, we used to occasionally attend a giant meeting at one of the large ISPs — Microsoft, Yahoo, and the like — and it always annoyed me to be presenting to or engaging in a discussion with a room full of a dozen people and having all of them there with their laptops open, clearly distracted and doing other work. I’m increasingly finding annoyance with the Zoom equivalent, which is being in a meeting or attending a presentation, but turning off your mic and camera. It’s impossible to know as the person leading the meeting or speaking if you’re actually there. And if you’re there, if you’re paying attention. And how many times in a meeting can…

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,…

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…

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…

How I Engage With The Chief People Officer

Post 4 of 4 in the series of 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 and Signs your Chief Privacy Officer isn’t Scaling. You won’t have a ton of time to engage with the Chief People Officer but there are a few ways where I’ve typically spent the most time, or gotten the most value out or my interactions with them. So, you’ll need to capitalize during those few moments when you do get a chance to engage with the Chief People Officer. I ALWAYS work with the CPO as a direct report.  No matter who my HR leader is, no matter how…

Signs Your Chief People Officer Isn’t Scaling

This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here) If you’ve been following my previous blog posts on the Chief People Officer you have figured out when to hire one and what to look for in getting a great one but even so, you can’t just assume that your Chief People Officer is going to be able to scale with your company. I have found that Chief People Officers who aren’t scaling well past the startup stage are the ones who typically operate in the following ways. First, a CPO might not be able to scale if they are…

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!

What Does Great Look Like in a Chief People Officer?

This is the second post in the series…. the first one When to hire your first Chief People Officer is here). While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything…

When to Hire Your First Chief People Officer

(Post 1 of 4 in the series of Scaling CPO’s) In most startups, the HR function starts out as tactical, because you have to get people hired and paid, and while you might have a founder or early-stage employee who can do these things, often these tasks are frequently outsourced to a PEO.  As the company grows, it probably in-sources payroll and benefits, hires a recruiter, and maybe has an HR Manager who handles the function. Depending on the number of roles you see being filled, the degree of specialization, or a host of other factors, an in-house team to handle the tactical aspects of HR makes a lot of sense. But at some point you may need to hire…

My Favorite Interview Question

I hosted a CEO roundtable dinner the other night, and someone in the group asked me what my favorite question was to ask in interviews. I kept thinking about something I read years ago, that the late legendary Zappos founder Tony Hsieh used to ask, “do you consider yourself a lucky person,” about which he said, “Lucky people approach the world with an open and optimistic mind that enables them to see unexpected opportunity more readily.“ That’s a good thing to find in a future team member of course, but the question is a little too indirect for me. My favorite question (ok, it’s a compound question) is to ask someone “What are you great at? What do you absolutely…