All those important lessons you learn over the course of a career can actually hurt you if you don’t know when to set them aside. You have to see when it’s not a time to be the seasoned CEO and instead lean into your role as the scrappy founder — even if this isn’t your first (or your seventh) rodeo.
Read MoreBeing part of building a seventh company taught me many things. It taught me that tech entrepreneurs can’t do everything — more than that, I learned that honesty about how your skills and expertise line up with what you’re trying to build is much more important than a passion for what you’re selling.
Read MoreIn 2005, I was working as a consultant, doing some due diligence on software for a startup. The company, founded by two patent attorneys, was attempting to create an online marketplace for swapping books, music, movies, and video games—back when those were all physical objects that needed to be physically traded. The founders had patented their ideas and written hundreds of pages of specs. They’d already hired, fired, and had sued one software development firm. When the second firm they’d hired went past budget on a fixed price contract before completing the software, the founders reached out to me.
Read MoreThe experience left a big impression on me. Leadership isn’t theoretical. There are real, perhaps even dire, consequences to poor leadership. Fudging it doesn’t work, and pretending that two wrongs add up to a right could end with you thanking your lucky stars that you don’t have to explain to your board how you blew up a BMW test engine.
Read MoreIt took me three years to go from VP Engineering to CTO to COO to CEO. How does someone grow that quickly? Yes, I worked hard and focused on results. Yes, I was afforded an opportunity being at a good place at a good time. Still, no amount of hustle, talent or luck could have made such a rapid transition successful. What made it possible?
Read MoreAs a leader or entrepreneur, you get to create vision, set goals, and define success. As a business coach, I’d be negligent if I didn’t say that money (revenues & profits) is important. A business needs to be able to sustain itself (and its principals, team, investors, etc.). To make money, we need people. To attract and keep people, we need team and well-defined values. There is a direct relationship between money, people, values, culture, and organization. Who you hire and how you lead and build team is critical to the long term success of anything you may undertake where organization is necessary.
Read MoreAmidst the tension, I was making every rookie management mistake in the book. Except I didn’t even have a book. I had no management experience and no training, nor did anyone around me. I made hiring mistakes. We were offered a course on Behavioral Interviewing, (which was the best thing I learned and saved my book, 20+ years later, pictured here), but even with the training, I put the wrong people in the wrong jobs. I recall my QA Manager being a disaster. There were other performance issues on my team. Wondering what to do when I found an employee sleeping under his desk. I didn’t know how to handle any of them. I tried to use my engineering skills to fix the problems, but you can imagine how that turned out.
Read MoreThe first lesson came from my time at KnowledgeSet Corp in the late 1980’s. KnowledgeSet (KSC) was a pioneer in the early PC days, one of the first to put data on a CD-ROM, before CD readers were standard on PC’s or windowed operating systems were the interface to your computer. The company was founded by Gary Kildall and Tom Rolander. It was a company of about 15 geeks - and I mean that with every connotation of the term.
Read MoreStartups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
I don't think every CEO needs to become a LinkedIn personality. The question is simpler. Who needs to know you exist? Where are they? And what would help them understand how you think before they ever sit across from you? That answer will change as the company grows, as your buyers change, as platforms come and go. You adjust. That I don’t think you can do anymore is decide visibility isn’t part of your job at all. Your personal brand is important to your company’s brand.
Most founders and executives I work with are uncomfortable talking about how they look. It feels shallow. Not the point. I get it. They started their companies because of a vision, not an ego. By the time they're working with an advisor, they're wrestling with real problems: who belongs in which seats, how to build accountability, how to run a leadership meeting. Thinking about personal image can feel self-indulgent by comparison.
Founders tend to think about a major transition as a singular event. You prepare, announce, close, and now you're a different company. In my experience, the company starts changing well before any of that happens. I've been through this several times now, and the details were different every time. The weirdness was pretty consistent.
Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Ask a room of leaders why they set goals and most will say accountability. That answer creates the problem. Goals exist for alignment. The company needs to reach a number, so this group does this, that group does that, and together the math works. Everyone is pointed in the same direction. Focus comes second. A good goal tells you what to say no to.
The instinct to build a team that moved in the same direction, at the same pace, with the same set of perspectives is limiting. Consistency is created at the expense of range. The goal isn't alignment of strengths. It's coverage. The most dangerous teams I've seen weren't the ones with conflict. hey were the ones with none. Where every conversation ends in agreement. Where nothing gets surfaced. Where the people who see things differently may have learned to stop saying so.
The same restlessness that makes it hard to stay on plan is what made them start the company in the first place. The wandering mind, the refusal to be satisfied with what already exists, the ability to see something before it exists: that's not a disorder. That's the source.
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I’ve been facilitating CEO peer groups for fifteen years. The biggest factor in whether someone gets value from a group is vulnerability. Not performative vulnerability. The kind that costs you something to say out loud, the thing you'd rather not say because it makes you look uncertain, stuck, bored, scared, or wrong. The people who get the most from these groups aren't necessarily the ones with the biggest problems. They're the ones willing to let the room see the problem clearly enough to help.