Benefits and pitfalls of engaging an advisor, hiring an executive or choosing a co-founder

Brent Lowe
6 min readJun 3, 2021


There’s a dangerous dynamic I’ve seen play out in many start-ups led by founders in their 20s and 30s. The consequences range from mild to catastrophic, from wasting time and burning through valuable resources through to sinking the business.

Here’s an all too familiar metaphor. The proverbial ship pulls up its anchor with the founder at the helm. The founder wants to travel far, fast. The waves swell. Lightning flashes on the horizon, drawing closer. The wind is blustering. The passengers stare wide-eyed, confiding under their breath, “we need more experienced people steering this ship.” The founder’s inner critic is questioning his or her abilities to captain a cruise liner. They haven’t even mastered paddling a canoe. They spot a smooth sailing ship in the distance and yearn to gain the experience of that captain. They fumble for the radio and utter a request which may land get them stuck sideways in the Suez Canal.

Entrepreneurs are hardwired to seek out accelerators and build momentum. How can I upskill? How can I position my company for success? And how can I rid myself of this sinking feeling that I’m one step away from a major screw-up?

There’s an endless supply of resources available for the knowledge-hungry. Podcasts, webinars, trusted friends and networks can offer a treasure trove of relevant and helpful information.

On the perpetual search for wisdom, there’s a particular resource that outshines others. While in most cases it’s beneficial and necessary, there’s no warning label or instruction guide included with this resource.

The quest for wisdom

What’s our first port of call when we don’t know something? We seek out someone else who does, and we draw on their knowledge and experience.

Entrepreneurs connect with advisors and employ experienced executives to quickly fill knowledge gaps. Some founders see it as a logical and natural step in business growth. For others, it’s an unavoidable and uncomfortable move. When done right, it’s thought of as the quickest and easiest route to bridging a gap. However, it’s not always smooth sailing. Painful lessons often accompany the journey.

Advisors and senior execs can be a ready and trustworthy source of insight. They help you build a business that has an impact. They support your role as a leader and offer many essential benefits. Here are 3 benefits and 3 pitfalls to be aware of when engaging an advisor, hiring an executive or choosing a co-founder.

Benefit 1: Advisors boost your passion

Finding someone who shares your passion can be a challenge. What makes one person tick can be completely uninspiring for someone else. Sharing, let alone influencing passion in another person, is a tall order. The right advisors and execs can provide fuel for the fire that’s already burning inside you, playing off your passion and acting as catalysts for great things.

Benefit 2: Advisors provide industry insights through experience and networks

When there’s something you need to know, an advisor is the one who has been there, done that and bought the T-shirt. They have closely followed the industry’s ebbs and flows for years. By tapping into their knowledge, you can move swiftly and avoid learning curves that could take weeks, months or years.

Rapid and productive business is built on good relationships. An introduction to advisor networks enables you to benefit from years of established personal history in the blink of an eye. This, in turn, means better traction in less time with clients, suppliers, media, and future talent.

Benefit 3: Seasoned executives provide proven leadership ability, varied life experience and helpful perspectives

Leading people is no walk in the park. You can watch as many TED talks as you’d like or spend every waking moment reading the latest books. There is no substitute for the learning that comes from doing. The appeal of engaging an advisor or senior executive is that they have lived leadership experience by the bucket-load.

We soak up knowledge through experience as we age. If you stand your 18-year-old self beside your present or 60-year-old self, each will be different. The process of living, learning and adapting is true for everyone. Advisors and execs enable you to assimilate different experiences and knowledge from a range of life journeys.

Exploring varied and contrasting ideas often sparks innovation and creativity. If you want to find better solutions, then it’s beneficial to surround yourself with people who differ in their thinking. Engaging advisors and execs who don’t tell you what you want to hear but challenge your thinking helps you recognize and overcome blind spots.

Pitfall 1: Conflicting passions

Advisors and execs often have strong opinions linked to their passions. It’s what makes them dynamic and successful. When there’s an alignment of passions, the relationship yields excellent results. When the passions that drive their opinions conflict with yours, it can be a recipe for disaster. A relentless and energy-sapping battle of wills ensues. The strong influence of passion on decision-making can easily be overlooked to the detriment of both parties. Alignment is vital, so seek out individuals who share your passion and purpose.

Pitfall 2: The experience and rear-view mirror traps

This is a migraine in the making. You’ve brought a senior person on board to advise you. You both know that they outrank you in terms of knowledge and years of experience. It’s difficult to avoid defaulting to simply following what worked for them before. Blindly trusting that your advisors always have the correct answer is a trap. They’re relying on past successes in different contexts to inform the present. In a business landscape that shifts rapidly, problem-solving skills should trump experience. Experience is merely a reference point for solving a current problem. It’s not a road map.

A close sibling of the experience trap is the rear-view mirror trap. Pushing boundaries and challenging the status quo is what makes entrepreneurs successful. Their perceptive nature and intuition enable them to sense opportunities that others are slow to see. Advisors tend toward more of a ‘rear-view mirror’ outlook, drawing on what worked in the past. In conversations with advisors, founders can avoid falling into a trap by listening for a balance between past proven methodologies and future-focused thinking.

Pitfall 3: The relationship and approval traps

We do business with people we know, like and trust, so a senior advisor or exec’s deep network is irresistible. All that glitz and glamour seldom yields the result you expect. Relationships take time and effort to build, often based on timing and context. Trap 1 is that you invest time and effort, and the network doesn’t benefit your business. Trap 2 arises when you become overly reliant on the network and use it as a crutch to solve your every problem. While drawing on the experience of your network can help you overcome challenges, it restricts new ways of thinking. Any value that comes from your advisors’ past relationships should be an unexpected bonus, not a default go-to.

Human beings are complex creatures with egos that need protecting and stroking. You’re human, and so are your advisors. A need to be liked can cause founders and advisors to fall into the trap of habitually agreeing with each other. Excessive flip-flopping on ideas is an early warning sign that you’re prioritizing popularity at the expense of healthy debate. You may both have off days when the ideas you come up with aren’t great. Having the freedom to engage in healthy debate is vital. To avoid falling into the approval trap, consider establishing an agreement up front on how you want your relationship to work.

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.

I help Founder CEOs of companies between 5 & 40 people who are experiencing early stage success and ready to scale — especially those wanting to build shared responsibility and accountability within their team. Click here to get your free copy of the 5 principles and 6 leadership roles for scaling a sustainable, prosperous company.



Brent Lowe

The Scale Coach for Founder CEOs and co-author of Lead Together: The bold, brave, intentional path to scaling your business