Not every new CEO knows where or how to spend their time. And just when they feel they're getting the hang of it, the job evolves and it's time to expand.
Leading a company of 10 employees is a lot different than leading a company with 150. As a new CEO with a bare-bones crew, you basically have your fingers in everything. You run product builds, handle security, conduct demos, oversee the deal desk, negotiate contracts, and take care of procurement. Added to that list are absorbing solo fundraising and recruiting efforts.
A company with a large workforce carries different demands. With the growth of our company, I now spend my time doing fewer, but much weightier, tasks.
I found the following helpful as we scaled from five to 50, and ultimately to 150 employees.
Let go, move up
When starting out as a CEO, I was responsible for everything from offer letters to sales calls. Today, we're hiring too many people for me to write offer letters. We now have a dedicated human resources (HR) team, and we also have an incredible head of sales. We have managed to replace the functions that I shouldn't be doing -- whether I like the tasks or not.
You have to be willing to make the best use of your time and be OK with giving things up. You also have to be humble enough to be willing to acknowledge when you're not a master in all areas of your business. But you also have to recognize that there are tasks that only you as the CEO can do. A few examples are: No one else in the business has the responsibility to successfully complete a fundraiser or recruit an amazing executive team -- that's on you (and these aren't easy things to do). Accounting wasn't my strength, so we brought in an amazing accountant early. Whether you're great at something or not, ask yourself, "Should I still be doing this?"
Let go and free yourself if you want to move your company ahead.
Invest in your leadership team
Trust your management team. I hired great leaders, some of whom I worked with previously and others who were new to me. In both cases, I immediately trusted them to get the job done. Since they were recruited for their expertise and talent, I knew I didn't need to spend time telling them how to do their jobs. Hiring this leadership team was one of my first big investments, and it has paid off enormously.
I encourage them to operate with high accountability, individually and autonomously, in leading their departments, and to work cooperatively with the rest of the management team. I don't need to be the bridge between functional areas because those relationships are theirs to forge. If someone has an issue with a peer, I expect them to talk and work it out. If they're solving a business problem that requires input from another department, they are encouraged to get it done. As a CEO, it's better when your management team is interconnected. I'm not just hiring people for their individual excellence, I am hiring collaborative leaders who can work as a team with (or without) my input.
When that happens, you build an environment of trust among leaders who can produce dramatic results. Nothing is more effective than a management team working toward the same goal and helping each other along so they achieve it collectively.
As such, I spend more time cheerleading others and focusing my attention on decisions that have the least certainty than on day-to-day departmental issues. If I'm doing my job right, most other decisions are made for me -- and they're nearly always the right ones for the company.
I like to say that today I only step in to make the toughest calls. My leadership team capably handles everything else, meaning that I only get pulled in on issues that might change the course of business today or in the future.
Remember your audiences
Since I raise capital regularly, I make it a point to speak with at least one new investor every week, and sometimes three or four. You never know who could lead your next round, so keep those channels open and you won't be looking for support.
You need to develop a rapport with your board, too. It can't just be about quarterly board meetings, you need to get to know each other as people too. While this makes board meetings less painful, which is a benefit alone, it also gives you the opportunity to get to know the people who are partnering with you on your business. Moreover, it helps you to understand what directors are seeing in the marketplace, trends in macroeconomics, future outlooks, and so many other things that help you operate as a CEO much more effectively. This kind of intel will not only prove useful, it'll also save you a lot of time.
Personally, I build rapport through text messaging. You might think it's an odd set-up, but think about it: Investors spend a lot of time in meetings, so it's more difficult to find time to chat via phone or Zoom. I also regularly have "casual drive-by calls" with my board members, but texting a question, gathering an opinion, or just asking them how they are doing and how their weekend was is a great way to create a lasting relationship.
The future is always calling
With more company growth, I am now a big believer in leaving sufficient time for the hard stuff. Why? Those are the decisions a CEO should be making. Every CEO worth their salt knows that reading, networking, thinking, and planning are some of the most critical tools available. I budget my time so that I'm able to be present for our employees and my direct reports, for our board and investors, and for prospective customers, all while still leaving time available to focus on envisioning the future.
We are a venture-backed company, and that means a key priority is figuring out when it makes sense to raise the next round of capital. Why? That's what we use to accelerate our business and continue our product development innovations. When you're pushing into a new phase of your business, you must reexamine everything from your expense structure to your infrastructure. You need to figure out what investments you have to make, how you'll build the right support structure, what functions must be added, and more.
Our growth explodes after each capital increase, and planning for this from a strategic standpoint is critical. How can we turn on the rocket boosters and push through the next series of milestones? What do we need to keep an eye on in the market? What are the trends going to be in six months, 12 months, or two years? What internal processes are going to break that worked well when we were smaller, but won't work now? (People often refer to this as scaling up.)
We look at everything -- how we onboard new employees, implement customers, handle key handoffs between departments, even how we plan office space and working environments. By the time the money hits the bank, if you're successful with an increase in capital, it's time to execute. The time for planning is behind you and you're now living in the future you just envisioned. The only person in the business who can really do this is you, the CEO.
Tactically, for me, that looks like stacking meetings on Tuesdays, leaving Wednesdays and Thursdays open for spontaneous needs, and saving Friday for deep work. Monday is about setting the tone for the week. I work to leave plenty of time to look forward, because that is ultimately one thing that I alone am responsible for.
If you budget your time wisely, it will pay off as you scale your company.