Startup Execution

Cheap Advice is Cheap

Back in 2001 when I was a first-time CEO, I struggled to grow the company to beyond a certain point. We had a good product that filled a very important market need, so the company quickly grew to over a hundred customers. But as we grew, we struggled to consistently provide the quality that led the market and fueled our rapid growth. We often handed large responsibilities to our employees that stretched them beyond their experience. Sometimes they excelled, other times they crashed and burned.

As we struggled to get over the hump, I sought advice from multiple people. I found no shortage of advisors who were quick to push solutions that were sure to solve all my problems. The challenge was, very little of the input actually solved any of my challenges. As I look back, the common thread among all the flawed guidance was the lack of investment to truly understand the problem and custom-tailor a solution that worked in my situation. Most advisors spent maybe five to ten minutes asking a few questions about the nature of our company’s challenges, then proceeded to give 30 to 60 minutes worth of “off-the-shelf” recommendations from their limited understanding of the problem. To say I was frustrated was an understatement.

But things changed when I sat down with Jenkin, an inventor with both a strong technical background as well as great startup execution experience. Jenkin asked me dozens of questions over a two-hour period. He listened to my responses, which often led to three or four more questions down a specific path. Once he had a good grasp of the problem, we spent the next hour brainstorming possible solutions. We worked as a team to craft some specific process changes, role changes and expectation changes. Unlike the quick hit, “drive-by” advice I received from others, Jenkin was willing to dive deep to truly understand the essence of the problem. He invested significant time in me and my company’s problems, resulting in tangible changes that helped us clear several hurdles.

From this, I distilled the observations below.

Details Matter

In most cases, the devil is in the details. Hard problems are rarely solved from the 60th floor of an ivory tower. You have to be willing to get down to the ground floor and dive deep into the problem to understand specific strengths, weaknesses, opportunities and threats.

Strategy and Tactics Matter

Most advisors and consultants prefer to operate at the strategic level. This makes sense as war strategy guides the overall campaign. However, great strategies still fail without strong battlefield tactics. Don’t assume that smaller startups with younger founders know how to implement good battlefield tactics. Don’t be afraid to plan out the details of specific battles to ensure the success of the larger strategy. This takes more time, but improves your odds for victory.

Execution Matters

Look for advisors with strong operational experience. In football, it’s great to have a wizard of an offensive coordinator who can craft fantastic game plans against your opponent. But without the offensive line coach to teach blocking technique, the receivers coach to teach route running, and the quarterbacks coach to build the ability to identify and exploit defensive sets, the game plan falls apart. If your offensive coordinator can’t also coach the fundamental skills, you’ll have to either supplement with other coaches or find a different person to lead your offense.

Size Matters

Startup execution is a very different problem compared to large company execution. Look for advisors who have successfully executed in smaller startup environments. Flying a Boeing 787 Dreamliner complete with advanced auto pilot and computerized navigation is a much different skill than racing a motorcycle down the speedway.

Go Deep

The startup community is full of people who have tasted some success. Many position themselves as advisors based on their past victory or victories. But just because someone is a great athlete who has won a few trophies doesn’t mean they are a great coach or take the time to give you great advice. When you compete at the highest levels, you need coaches who go deep with their understanding of you, your company, and your challenges. Quick, casual advice is cheap. Look for coaches that roll up their sleeves instead of pontificate. Team up with advisors that take the time to build a broad and deep understanding of your market and your needs — invest in advisors who invest in you. Success is within reach if you build a team of coaches who don’t just point the way but help you build the road to get there.


Startup Execution

The Teachable Student

A few years back, one of my friends in the venture community suggested that I connect with a young startup. He felt I would be a good candidate to advise the startup in their journey. I proceeded to meet with the founders and got an overview of their company and their plan. I asked several questions, probing for more insight where I saw potential areas of need. Every question I asked was met with a confident response. Never mind that the content in the response was lacking. I tried to graciously point out that I had some concerns about parts of their plan, but I received strong push-back, as they seemed offended by my suggestion that there was an opportunity to improve their approach. After several more rounds of back and forth, I ended the discussion and declined to advise their startup. I never heard from the founders again, nor can I find any trace of the company today.

Everyone needs help

In my 30+ years of work experience, one common trait of every founder, every startup, and every business plan was the opportunity to improve. No matter the depth of your education, the breadth of your work experience, or the strength of your pedigree, no one is perfect. No company has all the bases covered, no plan exists that couldn’t be improved. I chose not to advise the startup above because they worked so hard to appear to have no needs that it became clear they didn’t want help. Any effort to give them help would likely result in either subtle resistance or contentious debates.

Advisors by definition provide advice. But the advisee needs to at least be willing to accept the advice. In fact, a healthy relationship between an advisor and a founder is built not just on willingness to accept advice, but a strong desire to seek it out. Don’t make your advisor play detective to figure out how they can help. Don’t be afraid of looking weak if you have questions. A seasoned advisor and coach will not think any less of you if you admit you have needs. In fact, a really good advisor will love your transparency because it encourages teamwork and cultivates trust. When meeting with your advisor, don’t be afraid to come with a list of topics that you want help with.

Michael Jordan – GOAT

Many basketball fans consider Michael Jordan to be the Greatest of All Time. It should come as no surprise that Jordan said “My greatest skill was being teachable… I was like a sponge. Even if I thought my coaches were wrong, I tried to listen and learn something.” Watching Jordan play was a delight as he lit up the scoreboard on the offensive end while also winning Defensive Player of the Year honors. Many founders and executives would do well to imitate Jordan’s attitude and approach.

Humility to be Great

But to be clear, being teachable is not a technique. It is not something you just add to a meeting agenda in hopes of making a good impression. Being teachable is an issue of character. It is rooted in humility — which sadly is a word that is very rarely used among leaders today. The humble leader is secure enough in who they are that they don’t have to appear to know everything, aren’t enslaved to winning everyone’s approval, and aren’t afraid of looking bad.

Humility also goes both ways. Good advisors need to practice it as well. I’ve seen plenty of insecure advisors who are afraid to admit that they don’t have sufficient background in a certain area to provide worthwhile guidance. Be wary of advisors who cave in to the pressure to have an answer for every question. Such advisors are prone to give advice that may not be best for your situation. In the same way we’d question the qualifications of a single person who claimed to be a doctor, lawyer, engineer, scientist, astronaut, athlete and therapist, we should question any advisor who confidently pushes their opinions on every professional, technical and personal matter that arises in the life of your startup.

Greatness Through Coaching

Those who seek success are often encouraged to build a relationship with a mentor or a coach. Professional sports provide dozens of examples of great relationships between a coach and an athlete that clearly transcend a single game or team. Take a moment to read about John Wooden and Kareem Abdul-Jabbar, Gregg Popovich and Steve Kerr, Tom Izzo and Draymond Green, or Tara VanDerveer and Jennifer Azzi. Many athletes are obligated to work with a coach, but not all coach – athlete pairings result in sustained success and long-term relationships. In the same way, many startups are paired with advisors, but not all startup – advisor relationships produce great fruit.

Recognize that we all need help. Commit yourself being teachable. Seek out advisors that know how to advise. Install a culture of transparency rooted in humility. With this as a foundation, you’ll be well on your way to success in not just your startup, but in your personal life as well.