Being the Boss – There Ain’t No Classroom Instruction or User Manual

Mention you’re about to start a business and you’ll get plenty of advice. Everyone you know will suddenly turn into an expert on financing, marketing and sales strategies, technology and innovation. At least that was my experience.

But what you don’t hear is what it’s really like to be in charge, even if you’re the CEO of just yourself. Knowing the buck truly does stop with you is a subject that leaders and bosses rarely share. Some do, but not as many and they should, as it’s vital.

That’s where Jim Whitehurst, the president and CEO of Red Hat, one of the largest and most successful providers of open-source software, comes in. Before joining Red Hat, Jim was the COO of Delta Airlines, so you’d assume he knew exactly what he was getting into – but that’s not the case.

Here are some examples that Jim sights. Read on.

You will, in fact, still have a boss, in fact lots of them. Most people assume you don’t have a boss when you’re the CEO. If you’re the sole owner that is, strictly speaking, true … but you still have plenty of “bosses.”

And that means you have to consider the different objectives of all those bosses when deciding what to do. In certain cases there is a board, major investors, government officials (if a public company), Wall Street, employees – lots of bosses.

Having greater latitude is one of the fun parts of being a CEO, but never assume you’ll have free rein to do whatever you want.

The input you receive will often conflict. Some investors may want you to focus more on short-term results than longer-term growth. Different customers may want very different things. Even individual board members can have very different opinions and objectives.

Your job is to continue to tell the story of your company, continually make judgment calls, and continually balance personalities, needs, and goals. That’s one of the most challenging things about the job; since you have multiple bosses with multiple agendas, you constantly wonder, “Am I doing the right things?” (or doing things right?)

Sometimes you will have less latitude than when you only had one boss. When you have investors or a board or employees whose future is at least partly in your hands, even though you’re in charge, you sometimes (quite often actually) need to seek permission. And unlike when you had a boss, often there’s not just one person you need to ask.

Everything you do will be under a microscope. As a CEO or business owner, you’re constantly on display, not just for the job you do but for things like what you wear, whether you use a paper cup instead of a mug and what that says about your environmental consciousness, what kind of car you drive, etc.

For example, an employee was talking with my wife at a company event and said, “One of the things I really like is that Jim is family oriented. That’s important, because I have kids.” How did she decide that? During a meeting I took a call from my wife — she rarely calls me at work and I wanted to make sure nothing was wrong.

But what if for some reason – say I knew she planned to call at that time to leave me a message that wasn’t urgent and I had hit “Ignore”? Would that employee have thought I was not family oriented … and that Red Hat was not a family-friendly company?

Possibly so. When you’re under the microscope, it’s amazing what can be read into the smallest things. One interaction doesn’t necessarily send a major signal, but when your business is large enough and employees only see you occasionally, that one experience can form their entire opinion.

Being in charge is like a double-edged sword. You get to lead by example, but you can set tons of inadvertent examples. You can’t have a bad day.

You will be the worst boss you ever had. Becoming your own boss theoretically frees you from being controlled and micromanaged … but your conscience is probably the most exacting taskmaster you’ve ever worked for.

Take today for example, in theory I could have not scheduled anything, and just “goofed-off.” But almost all the individuals who make it to the CEO level or who start their own company are fairly competitive, driven to do well, committed to performance. They’re their own toughest boss.

While you do have more control, with that responsibility comes a sense of obligation that pushes most people harder than any boss possibly could.

Your job will definitely be different from what you imagine. I came to Red Hat thinking my job would be quite different than it actually is – not better, not worse, just different. Even though you’re given a title, you still have to earn trust, earn latitude from shareholders and employees … you still have to do all the things you have to do as an employee to gain credibility and respect.

Six years ago I came from doing an operations-intensive job in a low-margin industry. Red Hat is a high-growth company with incredible opportunities that result in incredible ambiguity – my job is a lot more about developing strategies, inspiring people, inspiring creativity, and pivoting from driving numbers and executing to something totally different has been an interesting challenge.

That can happen to you even if you start a new business. Many people tell me what they thought their business would do – and what that meant their role would be – turned out to be very different from what they imagined.

… But it will also be the best job you ever had.


MaxCo Advisors
November 18th, 2015


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