Lessons Learned

The biggest thing I have learned is that the team is much more important than the individual.  I have worked in lots of circumstances where a “hero” could save the day.  I have seen that be wrong now enough times to know better.

Here are some of the other things I have learned:

  1. VOC (Voice of the Customer) is critical.  Just because it is a good idea doesn’t mean anyone will pay for it.
  2. KISS (Keep it simple stupid) has a lot of validity.  Just because customers or investors want you to be something is not a reason to be something.  Stick with a niche.  Dominate the niche.  Then expand.
  3. Make mistakes early.  Trial and error is a valid way to learn, but it becomes harder to shift direction as time goes on.
  4. Hitting lots of singles makes a lot of sense rather than waiting for the homerun.  Know your place in the industry and optimize it.
  5. Everything takes a lot longer than you think.
  6. Passion is essential just don’t let it blind you to reality.  On the other hand, being an evangelist or early adopter is great…but very difficult.
  7. Surround yourself with very smart people that are action oriented.  You can have great thinkers in a big company, but not in a little company.
  8. Working in a start-up environment is very emotional (assuming you are committed to it).  You feel the ups and downs.  And, those around you may get whiplash from trying to keep up.
  9. Don’t expand too fast.  It dilutes your quality.
  10. Do it right from the beginning.  Think about process and culture and know what you want to look like when you grow.
  11. Communication is always key at any size.  Make sure everyone knows what you are doing and don’t forget to provide positive feedback and constructive and direct feedback.
  12. A good, motivational leader is important.
  13. Have a few (but very close) partners.  Signing empty agreements that no one commits to wastes everyone’s time and is useless.
  14. Never forget that features tell while value sells.  Too many people get caught up in the offering not what the client gets out of it.  If you can’t articulate the value, no one will buy it.
  15. It is a small world.  Network like crazy and help others whenever you can.

A few other general things that I have noted over the years include:

  1. Work is like training for a marathon.  You can’t sprint all the time.
  2. Know when to throw yourself at work and when to pace yourself.
  3. You can’t innovate if you don’t see the forest through the trees.
  4. Being happy is critical.  This means different things to different people.  To me, I have to be learning and being challenged.  I hate repetition.
  5. Take time to know people.  People quit or stay because of their bosses.
  6. Life is too short.  If you feel strongly about something, be a change agent to make it happen.  Don’t just complain…bring a solution to the table.
  7. You never know everything.  And, you can learn from everyone…both above and below you.
  8. Myers-Briggs and other frameworks are helpful.  Understanding the framework and motivations that people bring to the table is important.
  9. Use facts.  Focus on metrics.  Never assume without some rationale.
  10. 80/20 rule actually makes sense.  Don’t wait for perfect.
  11. The grass is not greener.  It is just different.
  12. Surround yourself by people that are smarter than you and work to eliminate the need for you and your role.  If you are doing the right thing, the company will take care of you.  (generally)

Another way to look at this is what I shared with my team in 2013.  This was my framework for them to know how to work with me.

 INTJ (Myers-Briggs)

  • This is my personality type.  I’ve found the descriptions of it a good framework for people to understand how I act and think.  I also try to understand my weaknesses here and work with them.
    • Key point – I’m generally introverted and need alone time to think through things.  I’m not a big group dynamic or social person.
    • Key point – I’m a thinker meaning that I prefer to hear the facts, assess them, then render an opinion.  Hence, I will often write things in an e-mail and then call a meeting.
    • Key point – I can be overly direct at times and not very good at sugar coating things.

Fail faster to succeed sooner (from IDEO)

  • I’m a big believer in making lots of little decisions and acting them out and then changing rather than analysis paralysis.
  • This is similar to the agile approach in IT.
  • This also means being flexible in our current environment as things are changing constantly.  I try not to fire fight, but it does happen.

Function over form AND form over function

  • Figuring out that something works is much more important than how it looks (initially).  But, while collaborating, sometimes you need to state what is a work product versus what’s a final document.
  • I will redline anything you send me so don’t take it personal.
  • Form matters for clients and final work products.  Run a spell check.  Add page numbers.  Think about how documents print.  Assume they might get forwarded around to people.  Make it self-explanatory.
  • It’s ok to be a bull in the china shop.  I didn’t believe the advice when it was given to me several years ago which said “if people aren’t complaining about you pushing them too hard, you’re probably not pushing hard enough”, but I think there’s some truth there meaning that you need to push for what’s right even if people are hesitant to believe.

Meeting notes

  • Just a pet peeve.  If there are a group of people in a meeting, you should take notes and share them with action items, deliverables, and owners with dates.  People otherwise forget and every meeting is revisiting old topics.


  • I live by my outlook calendar.  Schedule things if you can.
  • I will overschedule myself so if you ask for 30 minutes then you will generally be limited to that.  I will try to be on time to meetings to respect the person who’s in them.  This also means that if you run late or start late then I will get up and leave when it’s time to go to my next meeting (with a few exceptions).

Saying no

  • We can’t do everything.  Sometimes less is more.  I see my role to push lots of balls forward while having you guys help me drive certain goals to completion.
  • You should have a point of view on things.  If you believe it’s wrong, gather some facts and state your case.  You may not always “win”, but you should be clear on what you believe.  Or said other ways – be proactive not reactive or bring solutions not answers.
  • Just because someone asks you to do it doesn’t mean you just go do it.  Think about the impact on other projects and you may need to request some re-prioritization.


  • I try to remind myself that making assumptions usually makes an “ass out of you and me”.
  • I try to think in terms of the patient and the client.  I’m not a healthcare person by training, and I think that healthcare is overly complicated for the average consumer.


  • I’m a big believer that you need balance in your life.  You should take your vacation.  You need to take breaks.  Sometimes doing something different or reading something different will help open you up to innovation.
  • I try to find time to be with my family and may leave to do something with them and then jump back online or trade an hour during the week to do some work on the weekend.  I expect you to know what you need to get done and manage your priorities.  As a boss once told me, you don’t get credit for just showing up.


  • I don’t need big formal status reports, but I like to get a quick e-mail weekly about what your big activities are especially if I’m not involved.
  • If there’s something that goes wrong, let me know early.  No one likes surprises and in small companies like this things can spread quickly from one office to the other.


  • I will see almost every e-mail you send me, but I can tend to get behind and not respond to all of them.
  • Use the title to display importance, need to respond, and subject.  (If I’m scanning e-mail and you’re responding to an old topic with information about a new item in the message then please change the e-mail subject line otherwise it can get missed.)
  • If it’s critical and it’s been more than 48 hours, you should re-send it to me or call me or text me.

Social media

  • A good proxy for if I’m swamped or behind is my blog.  I usually use this to think about ideas and the market.  If I’m not writing out there, I’m way behind.
  • I usually share articles or other things of interest via Twitter or the blog.  You don’t have to read them, but it may be helpful.


  • I’m generally going to share more information, articles, ideas, thoughts, strategies then necessary.  You don’t have to react to everything.  Some of it is just for you to learn.
  • At the same time, feel free to copy me on things you are doing so I know what’s going on.  I sort my e-mail based on whether it’s just to me, to me as a group or whether I’m on the copy list.

Make decisions

  • If it doesn’t do any of the following, then just make a fact-based decision and keep moving forward (see #2)…note that this assumes you’ve done some research and/or talked to people to get the facts:
    • Risk killing someone
    • Put us at risk from a HIPAA or compliance perspective
    • Commit significant resources (dollars or people)
    • Break the law

This is a marathon

  • I’m don’t use a ton of sports analogies but after running three marathons, I can tell you this is a good analogy.  Sometimes you have to sprint and sometimes you have to do a long run, but you have to keep your eye on the ultimate goal.

Have fun (self-explanatory)

In general, I see my role to help you in several ways:

  • Get rid of roadblocks within the organization
  • Challenge your thinking
  • Help you prioritize
  • Give you opportunities to improve your career whether here or elsewhere

9 Responses to “Lessons Learned”

  1. KISS – I like to use “Keep It Simple Silly” – that way not to insult anyone’s intelligence 😉 I’m glad to see you’re doing well!

  2. I’m just getting around to reading this part of your blog. These are well articulated and were just what I needed to read this morning – particularly item #1 equating work to marathon training. Definitely bookmark-worthy…

  3. As a former mgt consultant, entrpreneur and brand marketer on my second trip in the health care space, I think you have captured many of the lessons I have myself learned in the last 25 years post MBA school. I couldnt have said it better. Too many people need to learn these lessons which are real, pragmatic and would help them keep their sanity and BP down in many otherwise chaotic instances.

    Comments on Product Mgt are also very good. I would aslo add:

    * develop a thick skin and a batting average mentality
    * conceptualize success on many levels…i.e. you will hit singles, doubles, sometimes strike out.
    * respect operations and line managers perspective, they are on the front daily…but dont let that deter you from looking at how to change things, improve things and in some cases, kill them off when they have outlived their time.

  4. Thanks for sharing! I am not starting a business now but it is something I have considered, and I forwarded this on to my brother in law who IS starting a business this year.

  5. This is bloody great. Emailing to a few folks inside our company.


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