CEO Time Management, v1.0

One of the most frequently asked questions I get from startup CEOs, especially the ones who have scaled their companies to the point where they no longer have a “functional” day job, is something along the lines of: “How should I be spending my time?”

If I were to give a smart aleck reply to that question, I’d likely blurt out something like: “Um, how about by doing things that will build tremendous value for your employees, customers, and partners? Oh, and while you’re at it, how about doing those things in a way that helps your company become profitable and self-sustainable someday?” Now while it might be fun to see the reaction on a startup CEO’s face to a snarky reply, (I mean who doesn’t need a little levity every once in awhile, right?), the reality is that for every startup CEO this “time management” question comes from a place of deep rooted stress and anxiety. Specifically, the stress and anxiety that they aren’t spending their time efficiently; that they aren’t focused on the most important things that a startup CEO should be spending her/his time on each waking hour of each day.

Fair enough. No jokes about simply “doing the things that create a really valuable business”. Actually, I have put a lot of thinking into how CEOs can go about answering this question. In this post I’ll outline a simple v1.0 framing of how CEOs might approach time management. This lighter weight version is geared towards CEOs early in that transition from functional lead-oriented CEO to full-time generalist CEO, or for CEOs generally grappling with the stresses and sleepless nights inherent in pre-profit startup life. In a series of later posts, I’ll unpack a few more layers that might help CEOs think about their job in a more detailed way. That “v2.0” level of guidance will apply to CEOs whose companies have moved to a point where the CEO job becomes more a multivariate calculus versus what felt more like simple algebra when the company was smaller with moving parts that were easier to manage.

A quick delineation between v1.0 and v2.0. Think of v1.0 as a company that has raised up to a “real” series A round of capital and has hired up to like 25–40ish employees, small enough that as CEO you still know everyone reasonably well enough to catch up with every team member at the company BBQ. For v2.0, we’ll consider life scaling from series B and beyond aka where the company BBQ gets a little more challenging in terms of being able to get caught up on what they’re up to outside the office.

Back to v1.0. Let’s define the term “functional” day job. This is the point when the CEO, (most notably a founder CEO, but this dynamic can also apply to CEOs who are hired into a startup), no longer plays the role of CEO plus a “functional” role like VP of Engineering, Head of Product, CTO, etc. Essentially, those other executive team (“e-team”) roles are being managed by other individuals, and the CEO’s job is to just be, well, the CEO. At this point, a simple outline helps CEOs think about how they might allocate their time in this phase of the company — focus on your Plan, People, and Powder.

Plan. “So what’s the plan?” You can almost hear everyone in your company asking that question from wherever they sit in the office. Your first allocation of time should go to mapping out your company’s strategic plan in sufficient detail. Yes, a “strategic” plan. This doesn’t need to be some big company process stuff that takes three months to create; this is what every company no matter their size needs to define in order to scale. Ask yourself what winning looks like for your company, and how you and the team are gonna pull that off? I’ll keep this in bullet format — it will be easier to read and visualize the pieces you need to spend your time crafting with help from the rest of your team:

• Mission, Vision, and Values. Define your company’s mission as “what” the company does every day (e.g. “Remind is building a communication service that makes it easy for teachers, students, parents, and administrators to work together”), your company’s vision as the “why” the company exists and your aspiration for the future (e.g. “Give every student an opportunity to succeed”), and your company’s values as those elements that anchor your company’s culture around how you all work together and how you serve your users, customers, and partners (e.g. “Be teacher obsessed, Create simplicity for others, and Find a way”).
• Goals. Define the metrics that matter for your business. If you are pre-revenue, map out those operating or “user” metrics that prove you are on your way to defining product market fit (and being able to raise your next round of capital, more on that below). Of course, the sooner you can create a dashboard that includes customers paying for something you create the better.
• Strategic themes and initiatives (or investments). These are the discrete areas and projects that your company is allocating big chunks of resources (primarily your people) to build, ship, market, sell, and support. Typically as a company you should have a short list (like some number greater than or equal to 2 and less than or equal to four) of strategic “themes” that span the entire company and that stand the test of time, like a year (or longer if you really have figured out your North Star). Under each of your company’s strategic themes you’ll be able to define strategic initiatives that support that theme over a shorter (e.g. quarter or two) timeframe.
• Roadmaps and tactics. This is where the strategic initiatives get unpacked into more granular detail over shorter periods. For example, how do the strategic initiatives you have defined for the quarter breakdown over the shorter sprints that your product, design, and engineering team are executing on together. Further, these roadmaps and tactics allow team members to craft details around the work they are focused on over these shorter periods. This is how you as a CEO can help your teammates connect the importance of your company’s big picture goals and strategic themes to the equally important efforts each team member puts forth on a daily basis.
• Timeframes. How far out can you see? A year is what you should shoot for in terms of strategic themes, but in some cases it might make sense to think of your company’s strategic path as a rolling six months (e.g. two quarters). Start setting quarterly goals as soon as you can, not because you are going public next week, but because it’s an important cadence to get the company moving on, especially to the extent it pushes down to the detailed work that comes out of your two-week sprints. The discipline of mapping out your strategic themes and initiatives, as well as your roadmap and tactics over 90-days and the related sprints is key part of where you should spend your time as startup CEO.

People. Who is gonna help you turn this Plan into a reality? Every CEO — even if they shed the CTO or head of product title — must maintain the functional role of Chief People Officer. Your Plan is a critical support layer here because without it you will be making organizational design and ultimately hiring decisions in the dark. Making the wrong people decisions can in the worst case be fatal to a company, but even when you survive them, they tend to leave a pretty big scar. Here are four pieces of the People puzzle you need to pay attention to at all times:

• Org design. What does the org chart look like for your company? What should it look like? Should it still be product / engineering heavy, or is now the time to start building out the business side by investing in marketing, sales, finance, and operations. As CEO you will find the urge to draw org charts randomly in your notebook, on a napkin, or on your kid’s arm. This is normal, trust me. Keep drawing those org chart drafts to help define how the team needs to evolve.
• E-team. Who are your functional or “department” leaders? Now that you have stepped out of a functional role (or you always were in the CEO role with no functional oversight), what types of people do you need around the table to help you build the next phase of the company? The slots that are easier to define are heads of product, engineering, and maybe marketing and finance/operations. Depending on your stage, a head of revenue (sales) might make sense. Per the paragraph above, depending on how you think about your org, the other topic you will wrestle with is how many people should be on your e-team? Some say less is more, which in general I agree with, but there are certainly stages when you might find other folks need to be part of the e-team, so go with the flow (or your gut) here.
• Recruiting, hiring, and on boarding. Be sure you are involved deeply with helping craft how your company recruits, hires, and brings new people into your company. Invest in a point person to help manage the broader scope of recruiting — it’s definitely a full-time job sourcing candidates and helping manage the process of bringing them through your hiring process. Your role in hiring will vary from being directly hands on for e-team or more senior hires to being a part of interview loops for other hires where you might be asked to “sell” a candidate or push on a line of questioning to help your hiring manager make an important decision. Finally, be sure to make time to be there as part of the on boarding process. Meet with new hires soon after they have settled in, answer any and all questions, and most importantly share the details around your company’s goals, strategic priorities, and long-term vision. It’s easy to assume that a new hire has absorbed all this by the time they get through the hiring process, but the reality is they haven’t. They’ll need to hear it from you and others often as they ramp up.
• People managers. Investing time with your people managers is perhaps the best people-related time investment you can make. There is research from Gallup to back this up, but intuitively we all know that developing a sustainable company culture that is anchored around people building relationships with one another forms the foundation that enables a company to deliver both near term results and outcomes important for the business but also long-term personal and professional growth for team members. In terms of your time as CEO, this means spending time 1–1 with your e-team, with the managers that your e-team manages, and any other team member who requests your time. These conversations are where the magic happens in company building so make sure you allocate the time they deserve.

Powder. As in “dry powder”. Or money. Or capital. Or whatever term you use for that stuff you need to pay engineers, designers, product managers, sales people, support team members, marketers, finance and operations pros, contractors, vendors, and anyone else who feels the need to be paid to work for you and your company. Without a doubt, a major part of a startup CEO’s time needs to be spent on fundraising. In fact, there’s never really a time when you aren’t fundraising (or at least heavily thinking about raising money) as a startup CEO because the last thing that can happen is for you to run out of “dry powder”. Do that and you’ll have a hard time keeping all those important people showing up to help execute your company’s plan.

Fundraising for many CEO’s is a pain in the ass. They hate it and would much rather be spending most (if not all) of their time on architecting their Plan and executing it with their People. Amen to that — that’s the fun of building a business and I truly get the most satisfaction as a CEO when those two important “Ps” of Plan and People come together in a powerful way. But, money is what makes the world go around, or at least allows a startup to grow into a big company that can impact the lives of many people and sustain itself profitably towards that endeavor. So when deciding how much time to spend on fundraising, here are a few questions to consider:

• How much should I raise? Go into every fundraise with the mindset that you’re going to raise as much money as you can. You need that mindset to offset the low probability of success that fundraising typically yields for ventures and to deal with all the “No’s” you are likely to receive. It’s always a happy outcome if you have to tell investors “No thanks, I think we’ve got enough money in this round.”
• How long should the money last? Give yourself at least a year, ideally 18 months, or get an even longer runway so long as you’re mindful of valuation and how big a chunk of the company you are selling. Essentially, you need enough time to prove the most important and “fundable” aspects of the Plan you and the team have crafted ahead of the next time you will be out raising money.
• How valuation sensitive should I be? See question number one above, and be less concerned about taking a little extra dilution in order to get a little more money (and time) to prove things out between now and your next fundraise. However, be mindful of your valuation on the upside early on in your company’s life. In some cases raising at a lower valuation (and therefore taking a little more dilution and/or a little less money given where you are in terms of proof points) gives you more flexibility to play out the future capital raises for the company.
• Play the long game. Every time you raise money be thinking several years down the road. Be sure you employ a good finance partner and pick your investors not just for this round, but for every round to come. On this note, you want folks that believe in you and the company so they will invest in future rounds. And even if their investment model is such that they are unlikely to invest pro rata in later rounds, you can tap them as advisors and friends that help you network to the right investors for your B, C and later stage growth rounds. Finally, remember that raising money is part art, part science, and a large part serendipity. There’s no exact formula and we all do our best given the unique environment that surrounds our company every time we raise capital.

At this point I can hear some of you asking: “Ok, so how do I know if I’m allocating the right amount of my time on the Plan, People, and Powder?”. You can probably guess that the answer isn’t as easy as simply spending a third of your time on each area every week, month, or quarter. There will be times when you need to invest more of your time getting your Plan wired together so it makes sense and so the team is excited to go make it happen. There will be other times when it feels like all you’re doing is working on your pitch deck and meeting with VCs (or at least emailing them to set up meetings or replying to diligence requests). Finally, there will be some weeks or months when you’ll wonder if there’s anything else you’re spending your time on other than meeting with your e-team members and recruiting new hires.

On this point let your gut be your guide. Jot down in a notebook every Sunday evening the three words Plan, People, and Powder, and in between each list the first two, three, or five things that pop into your mind related to each word. Because our brains work so well in unconscious mode, this approach can be a pretty organic way to help direct how much time you need to spend the coming week in each area. For a startup CEO, knowing what to be spending your time on the coming seven days of the week gives you a sense that you are at least balancing the high order bits as best you can. At least for those next seven days.