Entrepreneurs: 5 watch-outs before you engage an advisor or hire an executive (or choose a co-founder)

I’ve seen the same dynamic play out in every start-up led by a 20 or 30-something founder. Sometimes it’s fatal. More often it wastes valuable time and burns through precious resources.

Picture this. The proverbial plane takes off with the founder at the controls. The founder wants to get as high as possible, quickly. There is turbulence. A wicked storm is on the horizon. The passengers start to whisper, “we need more experienced people flying this plane.” Privately, the founder is questioning his (or her) abilities to fly a jumbo jet. He hasn’t even mastered flying a Cessna. He sees another plane further ahead on the flight
path and wants to gain the experience of that pilot. He grabs the radio and makes a request that he will soon regret.

There is a combo of naivety and enthusiasm that turn great ideas into growing companies. That enthusiasm is often accompanied by a need for speed. A need to learn fast and implement faster.

Entrepreneurs are always on the lookout for accelerators. How can I learn more? How can I boost the business? And how can I shake the feeling that failure is just around the corner?

There are piles of resources available to help. Books. Webinars. Friends. Networks.

And there is one resource that is alluring. It’s likely necessary. Unfortunately it doesn’t come with a warning label. There is no instruction guide to avoiding common pitfalls.

The search for wisdom

When we don’t know something, what do we do? We look for someone else who does and learn from them.

Entrepreneurs engage advisors. They hire senior executives. For some founders, its a logical and welcome next step. For others its a painful necessity. Either way its sold as a quick and easy fix to a knowledge or experience gap. When done right, it is. Unfortunately it can come with some painful lessons along the way.

The Pros

When done right, advisors and senior execs are colleagues you trust. They help you build a business that has impact. They support your role as leader and offer many essential benefits.

A Passion Boost

It may seem soft and unimportant, but it can be tough finding someone who shares your passion. And it’s not easy to influence passion in another person. Advisors and execs can feed your energy and play off your passion.

Critical Industry Experience

There are things you need to know and these people know it. They have been following the ups and downs of their industry for years. Their knowledge can save you weeks, months or years by helping you manoeuvre.

Valuable Contacts

Nothing moves business faster than good relationships. You will get traction faster with clients, suppliers, media, and future talent. You gain years of personal history overnight.

Necessary Leadership Experience

Leading people is tough. You can read as many books as you’d like. Ultimately there is essential learning that comes from doing. These people have been in the trenches.

Deep Life Experience (that differs from yours)

Face it. You know more now than you did when you were 18. You’ll know more when you are 60 than you do now. That’s how life works for everyone. Advisors and execs allow you to tap into the experience from a different life journey than your own.

Helpful Views and Perspectives

Creativity comes from playing with ideas. Surrounding yourself with people who differ in opinions helps surface better solutions. Advisors and execs who challenge your thinking help you avoid blind spots. Plain and simple.

The Pitfalls

Quite simply, we’re all human. With our humanness come challenges.

The Passion Trap

By their nature, advisors and execs usually have strong opinions. There’s nothing wrong with that. But when those strong opinions are anchored to personal passions that differ from yours, disaster looms. If I’m passionate about building a consumer business while a commercial business turns your crank, we will be in a constant tug of war. Every discussion and decision will become a battle between conflicting passions. The risk here is under valuing how much passion influences our decision making. The solution: Look for individuals who share a personal passion and purpose that aligns with yours.

The Experience Trap

This one is double trouble. You’ve hired a senior seasoned person to advise you. They have more experience than you. You know it. They know it. You both risk falling into the routine of following past experience. If you trust that your advisors always know the right answer, you’ve fallen into the trap. You are, in essence, outsourcing your job to someone else. Your advisors are relying on a fixed set of past successes to guide the present. The solution: Look for problem solving skills over experience. Past experience is a data point for solving a current problem. It’s not a road map.

The Relationship Trap

This is two potential traps in one. A stacked rolodex is an appealing reason to engage with a senior advisor or exec. In reality, it rarely pays off. We each protect the relationships we’ve worked so long to build. We only make connections when the timing and context is right. That’s trap #1: A rolodex that doesn’t materialize to benefit your business. Trap #2 is the exact opposite. Beware when your advisors gravitate to their rolodex to solve every problem. It’s easy to call a friend. And sometimes it’s the right thing to do. It also closes the door to new thinking. The solution: Reduce your expectations of the value that will come of your advisors’ past relationships. Consider any value your receive as a bonus.

The “Rearview Mirror” Trap

This trap is a close sibling of the experience trap. You are a successful entrepreneur because you push boundaries. You have an ability to sense opportunity long before it becomes clear to others. Advisors can have an over reliance on past and proven methodologies. They stop discovering and creating new solutions uniquely suited for the future. You are looking through the windshield while they are looking in the rearview mirror. The solution: Listen for how potential advisors balance their conversations between proven methodologies and new thinking.

The Approval Trap

Your advisors are human and so are you. You both have egos that need stroking and protecting. You may each have a need to be liked too. If you and your advisors are always agreeing with each other, you’ve both fallen into this trap. Healthy debate is important. You won’t always have the best ideas. Your advisors won’t either. The solution: Have a clear agreement up front on how you want your relationship to work. Watch for excessive flip-flopping on ideas at the expense of beneficial debate.

 

How have your advisors and exec hires worked out? If you’ve learned some lessons that can benefit others, I’d love to hear about them.