What do you do when you need to make an organizational change or let an employee down and you want to maintain a successful employer-employee relationship? For each situation, the first step is being willing to have difficult conversations with your employees.
Read MoreWhile some people may think the word is overused, the truth is: authenticity is in. Employees want it. Customers and clients want it. I’ve been inspired by friends and clients who’ve done the vulnerable work of being authentic even in the face of fear.
Read MoreGiven the bonds that can develop in the trenches of an early startup or young business, it’s not uncommon for business relationships to veer into friendship. What happens when a company grows beyond a person that helped start it? And what do you do when you’re the one faced with that dilemma — do you choose the business or your friend? Or is there some way to choose both?
Read MoreIf you’ve turned your nose up at the concept of psychological safety because, frankly, you’re getting tired of trying to figure out every new buzzword, I’m encouraging you to rethink. Creating a workplace culture where people feel safe to be themselves and feel respected for their contributions is critical. You’ll lose talent if you don’t.
Read MoreAs your organization grows, expands, and perhaps becomes entirely virtual, you’re having to find more ways to create those frequent touchpoints. Quarterly meetings are an excellent tool for communicating your vision and ensuring alignment on your team.
Read MoreWhat coaching style do you need to use with each of your team members? Just like you probably have a coaching style you’re most comfortable with, each of them also has a style of being coached that’s most effective for them. You have to coach the people who report to you, so as a leader and a coach, you may have to get comfortable with different styles of coaching.
Read MoreGetting good at giving effective feedback is one of the most important parts of leading — right up there with learning to delegate. Having those conversations, sometimes difficult, is crucial to their development and to your organization’s success. Here are our tips for doing it well.
Read MoreIf you’ve worked with a good coach, you know how transformational the process can be. Your employees need that experience as well. They’ll grow, be more engaged employees, and become happier. Your business will be all the better for it.
If you’ve just seen yourself as their manager, you’re missing out on a big opportunity. Actually, a big requirement. Now more than ever — when people are changing jobs at an alarming rate and everyone’s reeling from all the uncertainty in our world — you need to keep your employees engaged.
Read MoreSince I began Trajectify, I’ve had the opportunity to coach a number of family-owned businesses, from intergenerational companies to husband-and-wife teams. In some ways, they face the same challenges as any other business. They have to figure out how to maximize their cash flow, hire the right people, and scale their business.
Family-owned businesses also have their own particular set of challenges.
Read MoreWhat does it take to cross that golden line? We sat down with three long-time Trajectify clients to talk about how they became multimillion dollar businesses and what other entrepreneurs can learn from their success.
Read MoreSome founders reach a point where they need to move beyond their MVP and provide greater value to their customers. Let’s talk about how founders often end up in a technical cofounder search, the problems with that approach, and what you can do instead.
Read MoreBefore we can move past our fear, we have to become detectives. We have to find our fear. Identifying our limiting beliefs is one of the most effective ways to figure out where the fear lives and then flush it out.
Read MoreSome of the distractions are new. The quest for productivity isn’t. Managing your time better (and thus reaching your goals more efficiently) is about developing two things: (1) self-awareness and (2) structures to support you.
Read MoreWhen you’re going it alone as a founder, you might be missing some critical personal elements of running a business. And the absence of those supports can lead to loneliness.
Read MoreThe CEO rulebook is completely different from the founder rulebook. And once you’re not a startup anymore, you can’t keep acting like one. If you do, you’ll risk the success you’ve worked so hard to achieve.
Read MoreWhether you’re creating a full-fledged training program, helping a few high-potential individuals, or support a recently promoted manager, you need four things to support their development.
Read MoreEvery organization has a culture, whether it was created intentionally or not. Developing and implementing your values puts you in control of that culture. Most importantly, it helps you identify who’s aligned with it and who’s not. Here’s how to create your core values — not just some words that you put on a wall or a website — but the actual tenets that underpin your organization’s culture.
Read MoreAt some point, that do-it-all person will have to stop doing and start delegating. Otherwise, they’ll begin to feel like they’re on a hamster wheel — doing what they’ve always done but suddenly getting nowhere. Making that shift is challenging. In fact, it’s one of the most difficult, yet important, transitions founders go through.
Read MoreThe concept of a coach used to be reserved for athletes. Now you can hire a coach to help you with everything from weight loss or parenting to public speaking and career transitions. So with all these coaches running around, how do you know what’s a worthwhile investment of your time and money?
Read MoreAll 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 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.
TEAM | INTERIM EXECS | COACHING | PEER ADVISORY | SERVICES | RESOURCES | CAREERS | CONTACT
Copyright 2026, Trajectify LLC. All Rights Reserved.
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.