It looks so easy. There is low hanging fruit everywhere. In fact, there’s fruit all over the ground.
There are no systems. No structures. No guidelines. The team is running hard and fast, seemingly in a state of chaos.
Welcome to your early stage entrepreneurial adventure.
To a seasoned executive with years of industry experience, this can look like a piece of cake. It’s an opportunity to make a real difference and fulfill those entrepreneurial urges. You can have a big impact and boost this company to the next level.
You are ready to leave the safety net of Goliath for the challenge of fighting along side David.
The idea of joining a startup is sexy. It’s alluring. There are stories of pending industry disruption, untapped market opportunity, mushrooming prospect lists. You can taste the freedom, clear of senseless bureaucracy.
How do I know this? Because I’ve had this conversation more than a hundred times with executives. Successful and talent people who were planning to jump on board with an entrepreneur. Earlier in my career I hired many of them into their roles. CXOs. VPs. Super-talented industry specialists. Unfortunately I consoled many of them too on their way out.
There are three mistakes that executives make heading into their new entrepreneurial roles. For most executives, starting with an early stage company is like falling into a cookie jar. You are full of energy and ideas. You want to prove your worth, and so you get to work. It’s understandable. And it’s a path to failure. Here’s why.
White Knight Syndrome
Coming into a founder-led organization for the first time, you have blinders on. You don’t know what you don’t know. And that’s a dangerous place to be. The risk is that you appear like the White Knight who is riding in to save the day. You’ve done this work before and succeeded. Thus you are smarter and more skilled. You can fix them!
The reality is that you have more to learn from your new colleagues than you have to offer.
There is a danger with low hanging fruit. Those simple problems that are calling your name? They might be an easy win for you. A quick fix might be what’s called for. Or it might be the first of many potholes you fall in to.
In fast growing companies there is always more to do than time allows. The risk is that low hanging fruit becomes a distraction. You take your eye off the larger and more urgent issues that don’t have a quick or easy solution. For those accustomed to systems, processes, and guidelines, their absence can be frustrating. Fixing these gaps looks like the logical next step. In reality, the benefits of these fixes are often small.
Entrepreneurs have learned this lesson. They have little patience for what appear to be ‘make work projects’. They choose to leave low hanging fruit alone and focus instead on impact and results… the hard stuff!
The antidote: Commit to being curious for your first 3 to 4 weeks. And let the team know that’s your plan so they don’t expect decisions from you. Spend time asking questions. Why is there fruit on the ground? What has the team tried in the past? Why is the importance of one thing ranked over another?
In the early days of joining the team it’s easy to see everything that’s wrong. The mistakes can be glaring.
The company you are coming from did things better. You’ve seen and experienced smoother running operations.
Relationships are rarely built on criticism and condemnation, no matter how well intended. Before you joined, the founder and team fought endless battles together. Many mistakes were made and many lessons were learned. The team needs recognition and appreciation for everything they have achieved so far.
The antidote: Look for opportunities to recognize the work that created the company. Ask for stories about the early days. Find out about the most painful parts of the journey. Congratulate the group for making it through those tough times. Acknowledge the learning that the team has experienced. And do it sincerely.
Failing to understand your boss
Thankfully entrepreneurs are wired differently. Without entrepreneurial thinking our world would lack many great achievements. Entrepreneurs’ talents are critical to the initial success and ongoing survival of their companies.
Although each entrepreneur is unique, many share common characteristics. Unfortunately, for new comers to the entrepreneurial world, this difference is often not clear.
Entrepreneurs have immense drive and a deep desire to be successful. They have strong opinions. Breaking rules is part of their DNA. They are innate and fast learners. And chances are, they are unlike anyone who managed you in a larger company.
Entrepreneurs are also decisive. Once they make up their mind about your value to the company, it is not easily changed.
The antidote: Invest more time than you think is necessary getting to know your boss. Build rapport. Make it clear that you want to know when you piss off your boss. Spend time with your peers and anyone else who knows the boss well. Figure out who is thriving and who is struggling in their relationship with the founder. Then find out why. Most importantly, become comfortable early on with one critical realization. Despite your best efforts, your boss is not going to change.
Entrepreneurial companies can be a ton of fun. They benefit greatly from the knowledge and experience that senior leaders bring. The key to your success will be avoiding the potholes that are difficult to see.
Beginning your journey as a senior leader in an entrepreneurial company and have questions? Send me a note and I’ll share some more tips to help you be successful.