Category

Management

Signs Your CFO Isn’t Scaling

Post 4 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO, When it is Time to Hire Your First Chief Financial Officer, and What Does “Great” Look Like in a CFO?) While all the functions of a team are needed, perhaps the most critical function to make sure your company is able to scale is the CFO. Cash flow, investments into the business, compensation, budgets—nearly everything that happens in a company flows through the CFO—and it should. So, getting this role right is one of the most important tasks of any startup team. But how do you know if your CFO is up to the task of scaling? For CEOs, one…

What Does “Great” Look Like in a CFO?

Post 3 of 4 in the series on Scaling CFOs – other posts are How to Engage with Your CFO and When it is Time to Hire Your First Chief Financial Officer.)  A lot of startups have a bookkeeper, accountant, or even a spouse of a founder or employee handle the finances when they first start out, and that’s fine. But at some point you’ll want to hire a CFO and if you’re dealing with a lot of chaos it’s easy to think, “well, anybody is better than what we have now.” But I would hold off on that thinking because the CFO, a great one, will do a lot more than just manage the finances, AP, and AR. A…

When it is Time to Hire Your First Chief Financial Officer

(This is the second post in the series…the first one on How to Engage with Your CFO is here.) What comes before a full-fledged CFO?  Lots of startups have nothing more than an outsourced bookkeeper or one junior staff accountant.  Sometimes a founder or a founder’s spouse even steps in on this front.  As startups scale, they are likely to hire a more senior accountant, maybe an AR/AP/Collections staff member, or even a Controller or VP Finance. Depending on the complexity of your business you might be able to hold off on hiring a full-time CFO, but if you have any of these signs then it’s time to start thinking about bringing someone on board. One sign is intuitive, and…

Offsites in the age of COVID

I attended two offsites in the last two weeks – both great in terms of seeing people in person.  Interesting how differently they handled COVID protocols, although they were different groups with different vibes. One was a CEO conference for one of my VC’s portfolios.  There was a huge emphasis in all the pre-conference comms about COVID.  And lots of testing.  We all got mailed a very sophisticated in-house PCR test ahead of time to take and photograph/upload, complete with chemical reagents and some kind of centrifuge.  Then those of us who flew in for the event had to do an on-site rapid test before entering the opening reception and even had a side room to sit in for 15…

How to Engage with Your CFO

It’s fairly rare in a startup or scaleup that you, as a CEO or CXO (Chief [fill in the function] Officer) of any kind, will have significant one-on-one time with other members of the executive suite; instead, you’re most likely to spend time with the team in executive meetings, at offsites, or during all-company events. So, when you do get that one-on-one time it’s important to make sure that it’s not only productive, but that it builds a stronger relationship between you and the other person. As a CEO I learned that the best way to help people grow and develop, and to further develop a better understanding of each other, is to engage with them in a mix of…

Signs your critical functions aren’t scaling – three webinars

This is a topic we write about obsessively in Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams — in fact, it’s basically the whole point of the book! I’ll write some more specific posts here in the coming weeks that take some excerpts from the book, but Bolster is putting on three free and open webinars we’re calling our “Bolster-up Series” over the coming weeks that I want to share with everyone who reads StartupCEO.com. In this series, I’ll be doing short interviews with CEOs who we work with at Bolster on the different aspects of scaling specific functions, how they diagnosed those problems, and how they leveraged on-demand executive talent to solve those…

How to get the most out of working with a CEO Mentor or CEO Coach

(This is the third in a series of three posts on this topic.) In previous posts (here, here) , I talked about the difference between Mentors and Coaches and also how to select the right ones for you. Once you’ve selected a Mentor or Coach, here are some tips to get the most out of your engagement. Starting to work with a CEO Mentor is fairly easy. Give them some materials to help understand your business, and then come prepared to every session with a list of 1-2 topics that are keeping you up at night where you want to benefit from the person’s experience. Kicking off a CEO Coach engagement is more in-depth. I always recommend starting to work…

How to Select a CEO Mentor or CEO Coach

(This is the second in a series of three posts on this topic.) In a previous post, I shared the difference between CEO Mentors and CEO Coaches. I’ll share with you here how to select the Mentors and Coach who are right for you.  First, you need to find candidates.  Whether you’re talking about CEO Coaches or CEO Mentors or both, getting referrals from trusted sources is the best way to go about this.  Those trusted sources could be your VC or independent board members, friends, fellow CEOs — or of course Bolster, where we have a significant number of Coaches and Mentors and have made it our business to vet and vouch for them. Selecting a CEO Mentor is…

Addicted to Ruthless Efficiency

Last week I wrote about The Tension That Will Come With the Future of Work.  No one knows what the post-pandemic world of office vs. remote work will look like, but there are going to be some clear differences between how people will respond to being in offices or not being offices going forward.  As I said in that post, I think the natural, gravitational pull for senior people will be to do more remote work, because of a combination of their commutes, their personal time, their work setups at home, and their level of seniority…but with the possible exception of engineers, “all remote” may actually not be in the best interest of a number of junior or more introverted…

The Tension That Will Come With the Future of Work

The Tension That Will Come With the Future of Work A lot has been written about the Work From Anywhere life that knowledge workers are leading right now due to the pandemic, and what will come next.  Fred has a great post on it, and I’m curious to see how his and Joanne’s “Home Office Away From Home” space called FrameWork does when it opens.  In that post, he references a few other posts and articles worth reading: Imagine Your Flexible Office Work Future – Anne Helen Petersen We’re Never Going Back – Packy McCormick The Future of Offices When Workers Have Choice – Dror Poleg Instead of entering the debate about what the future will look like, which no…

Soliciting Feedback on Your Own Performance as CEO

(Excerpted from Chapter 12 of Startup CEO) As a CEO, one of the most important things you can do is solicit feedback about your own performance. Of course, this will work only if you’re ready to receive that feedback! What does that mean? It means you need to be really, really good at doing four things: Asking for feedback Accepting feedback gracefully Acting on feedback Asking for follow‐up feedback on the same topic to see how you did In some respects, asking for it is the easy part, although it may be unnatural. You’re the boss, right? Why do you need feedback? The reality is that all of us can always benefit from feedback. That’s particularly true if you’re a…