On Leadership Must-do’s
Alexis Rask, Partner
The coach with shared context; a former startup leader who knows what it takes to build and scale companies.
Being a founder is incredibly difficult and often lonely even while being fun and exhilarating. You need to be “something” for everyone - your team, your investors, your customers, your family and friends. Everybody has an opinion about what you should and should not be doing with your business and many think they have the answer because they’ve either been a founder before, have invested in something similar, or know someone who’s started a company in the same space. How do you wade through all the signals and noise to hear your own intuition and clarity?
I’ve spent so much time with founders over my career, both as COO and CRO but also as an executive coach to many Silicon Valley leaders. And one of the most salient things in my experience is as a founder, YOU are running your business today, in this year, with this team, building this product and in this market. That’s not the same as anything else that’s happened before. Therefore, the best thing that anybody can do for you is to share their perspective from their own experience and let you decide what to do with it. You can take input, and then go about discerning what’s relevant to you and what’s not.
What I’ve seen truly move the needle for entrepreneurs is having the time, space and mandate to solve the hairy problems and questions that otherwise keep looming in the background.
In my own experience as COO/CRO at shopkick, everyone we came across thought we should be selling our user data in some way - giving it out to the advertising tech exchanges. But we knew it was our strategic asset to protect and would be our mechanism for monetization. I had to listen to my own filter on the advice and make a tough call. We ultimately commanded a $10.00 CPM vs the mobile standard $0.10CPM.
Prioritize but make sure you’re prioritizing against the right goals.
You will always have too much to do with too few resources and too little time and it’ll always seem like you have to do all those things at the same time. This topic has been covered ad nauseum and you can find yourself so many tools and frameworks that can help you prioritize. Many of them result in ‘ordered’ lists according to importance and urgency, but it’s so easy to get a false sense of accomplishment when you’ve crossed everything off your lists. The tools address bucketing but don’t address thinking about which goals and which scope to optimize for when you’re coming up with your lists.
One item on which I’ve coached many founders is how to reframe and manage board meetings. Often you’re spending 10 - 5050+ hours, preparing for a 5 hour meeting, mostly presenting the board with a health report because you think that’s what is expected of you. Everyone, including your board, wants you to be focused on the business and so they also want the meeting to help you make key decisions that will drive the business forward. Now of course they still want to know how you’re doing, so designing a board meeting that allows you report on progress while truly enlisting the insight and experience of what is most likely a very capable group of people is the best thing you could be doing for everyone. If you can re-use the materials in a way that drives core metrics, even better.
Know when to be arrogant and when to be empathetic.
When you make a conscious effort to ask great, open ended questions with genuine curiosity, amazing information reveals itself. So often this new info is what can help avoid blind spots, clarify better decisions, uncover new options, negotiate more effectively, or collaborate more productively. It’s what can help a founder make a tough call or set a strategic bet. So what is an open ended question, anyway? Here is a way to parse using questions as the ultimate tool for success.
Closed ended questions - have a binary or yes/no answer.
Example: “Do you think it’s important to focus on growth?”
Leading questions may sound curious, but are actually steering the responder in some particular direction.
Example: “If we focus on viral hooks, how will that impact growth?”
Open-ended questions that are truly curious, ones where you have no idea what the answer will be and where it will take the conversation.
Example: “What could we do to impact growth? What are the pros and cons of each option?”
Of course, you’re going to get so much input from so many places on most things you do. One of the areas founders have to master is balancing the tension of when to integrate or ignore advice. So the skill to build is how to ask open questions that truly seek information over advice.
Master telling your own story.
How do you tell the story of why you do what you do, what it is, and how you do it? And in that order! Telling your own story is far more important than you can imagine. I even believe it’s mission critical. It’s important for inspiring people to join your team, for investors to take a chance on you, and for that first customer to pilot your product. I’ve even heard many investors tell me that they won’t invest money in a founder that can’t tell their story effectively. So spend time thinking about and testing your story with people you trust who will be honest with you. And if you don’t know how to do it yourself, seek help to create a succinct and digestible story that captures the essence of what you do and who you are, uniquely.
Get yourself a coach.
One of your main roles as a founder is to uplevel your organization and everybody who works with you to help your company mature. In order to do so, you also need to find ways to uplevel yourself. After 12 years of elbow grease and “Fake it till you make it” running startups, I got myself a coach that helped me do that exact thing. It changed how I approached everything. I stopped trying to design growth plans around the metrics others wanted us to hit and started designing plans around amplifying our strategic assets. I made some key team changes that has long been percolating in my mind but I wasn’t sure how to organize around. And we hit our highest revenue milestones as output.
A coach can help you think through some of your hairiest challenges, help you identify blind spots, and work on strategies to address them. That leaves you far more prepared to navigate unknown areas. You now have greater self awareness and a totally candid sounding board to talk through major decisions and dilemmas. That’s what I’ve had the privilege to do for many entrepreneurs.