Thursday, November 10, 2022

What to do in an Impossible Situation

Somehow I've already given this advice twice this morning so I figured I should write it up.  Enjoy!

There are times in your career that you will find yourself in a seemingly impossible situation.  You are handed a poorly conceived problem to solve with too few resources and time.  Things don't make sense, pressure is high and you are letting it eat at you.  Your work satisfaction plummets, your sleep and relationships suffer, you begin to question your very existential worth and/or start looking for the exits.  Sound familiar?  If so, then you have three choices when coming up against an impossible situation.

1.  Internalize it.  This is what you are probably already doing.  You fail to realize the situation is impossible and so you think you are the problem.  If only you were smarter/faster/taller/better looking you could solve the problem.  So you beat yourself up, internalize the insanity and start looking around for a savior--someone better who could fly in to save the day.  Stop it.  You are the right person for this situation. Why do I know this? Because you are taking it personally and have not quit yet.

2.  Quit.  This is always an option, and often the right one.  Some situations are so poorly conceived, driven initially by fear and ego instead of strategy, that not making them your problem (any longer) is the right idea  But if this essay speaks to you, it is because you don't really want to quit.  Whether it is your ego refusing to let you quit, your belief in the importance of the problem you are trying to solve, or both, you are in it.  You are not alone in your indecision. So be in it.  Just remember the sage advice from the Eagles: "So oftentimes it happens that we live our lives in chains...And we never even know we have the key."  If you do quit, quit well, with grace, gratitude, allow appropriate time for transition and do not place blame or burn bridges. How you do anything is how you do everything.

So if torturing yourself is not working (duh) and you are not going to quit, what can you do?

3. Change the rules.  As usual, science fiction shows us the way. When you are up against an impossible situation, you must first realize that the game is rigged against you.  This is important because it will help you STOP internalizing the failure and the injustice is often enough motivation to not quit.  Once you know the game is rigged, you also know that the game is open to rigging, so start rigging in your favor. 

First, change your definition of success.   Abandon notions of a perfect game and try to get out alive.  It will do wonders for your ability to problem solve.  Next, treat the current impossible situation as the first step in fixing the larger system that created it.  First stop the bleeding--figure out how to make your situation non-catastrophic long enough to go solve the real problem.  Third, start investigating (data helps, conversations are better) to find the real problem wherever it lies.  Protip: the problem always lies with someone who has more power than you, outside of your sphere of control.  Fourth, once you realize how the game is rigged, build a coalition to solve the larger problem. It is crucial that you abandon the mindset internalized failure so that you can abandon the whiny, self-pitying "I statements" and instead make inspiring "we statements."  

And if that fails, you can always quit! 

Thursday, September 29, 2022

Evaluating a Company to Join, Culture: Your Manager

Ok, back from vacation including but not limited to a wonderfully brief bout of COVID (first time!) and transitioning back into the school year.  Also, Wendy got a new role within SCAN, congrats to her! Where were we? Right!

While your senior leadership will ultimately determine the fate of your company and therefore your long term financial success, your manager will greatly impact your daily experience of work.  It is this daily experience of work that is so crucial for your mood, health, growth and development.  A bad manager can lead to burnout, poor work experience, stress and ultimately separating from the organization.  But a great manager can do something special, they can help bring joy to work, or at least help you develop toward what you ought to be doing.  Fortunately for me, my manager thinks about these things too.  

There are a few key qualities that you should interview for in managers:

  • Trustworthiness:  Does your manager do what they say they are going to do? Do they keep their promises?  Great, do the same and keep this person in your life forever. If not, run.  Do they keep promises to you (while you are favored) and break them to others when they are not? If so, run faster!  Life is too short to work with people you do not trust. 

  • Receptivity to feedback: No one is perfect. Every employee including a CEO, senior leadership, manager - has flaws and areas for improvement. A manager who listens to your feedback shows that your perspective is valued. It also indicates a willingness to absorb differing opinions to then make an educated judgment when a decision needs to be made. This doesn’t mean you’ll always agree on a topic, but healthy debate should be welcome because that means there is trust in the relationship.

  • Listening:  Sometimes you need to kvetch, and your manager needs to listen and take no action. Better it goes to your manager than erodes morale on your team or sets you up to look bad in the organization. Protip for managers (and all humans): just listen.

  • Results orientation: The purpose of work is to get things done. Ideally great, productive things that have a massive impact on the world. Results allow you all to focus as objectively as possible and ensure you aren’t kidding yourself that effort alone is enough.  Plus, with great results come great celebrations!  

  • Developmental orientation: Your manager is in the best position to help you become the best you you can become.  The best managers are ones who genuinely care about you and have the skills to ensure you evolve in your career. They encourage your strengths to flourish while sharing constructive feedback on your weaknesses.  They find ways to plug you into situations that give you the experiences you need. 

  • Advocacy: A great manager absorbs blame and shares credit, advocates for their team to receive appropriate recognition and reward, and does so in a manner that aligns company success with team success. They build peer relationships that allow work to get done smoothly and successfully.

These are just a few of the most important traits of great managers.  Much has been written on the subject and should be read by the managed and managing.   Be bold in interviewing your manager, they will make all the difference!

Up next will be a look into the business fundamentals to help you evaluate a company to join.

Friday, August 19, 2022

Evaluating a Company to Join, Culture: Senior Leadership

Choosing a company to join can be a worthy challenge.  Fortunately for all of us, Wendy Zhao has kindly agreed to collaborate on this next part!  Welcome Wendy!

While the Culture of a company may be codified in its mission and values, it is expressed through its people.  The people in a company obviously literally make up the company and two groups have an outsized impact on the experience of the culture: Senior Leadership & Your Manager. With this piece we are going to share how to evaluate Senior Leadership.

Senior leadership, the people with the Cs in front of their title, are directly responsible for the culture of an organization. These individuals set the rules for the company, hire / promote / fire, decide how the organizational structure evolves, determine compensation, and communicate the stories that carry the company’s culture and identity to employees, customers & investors. All sins of a company are sins of senior leadership, so it is worth understanding who you are signing up to work for. 

In the dynamic & ever changing environment like a startup, here are a few critical cultural components to look for in a leadership team:


The most important trait of a leadership team is cohesiveness.  With Cohesiveness, the company can flouris; without it, the rest of the company will be locked in a forever war of working long, frustrating hours with little getting done. By contrast, a leadership team that works well together and is aligned on the company’s mission will allow complex, integrated work to proceed smoothly.  They will be able to engage in healthy conflict to arrive at mutual commitment, hold the company accountable and ultimately deliver results. This is perhaps the best internal predictor of forward progress.


Startups are, by definition, trying to do something new while working with limited resources. They should be constantly forming hypotheses, testing ideas, evaluating feedback, learning the right lessons: iterating their way to understanding their customer, business & product.  You want a leadership team with the level of grit and resourcefulness to find the cheapest AND quickest way of doing something without compromising quality. Instead of hiring a costly consultant, ask a friend-of a friend-of a friend with subject matter expertise for a favor.  This way of getting things done is crucial in the early days and the spirit should never quite leave; however, it may be a shock if you are used to a more formal, process driven environment.  Your interview process is a good indicator here, how did it feel in terms of speed vs. polish/formality.  If you liked the speed, good. If you were put off by the lack of polish, you might have trouble once you work there.

Emotional intelligence

A CEO with strong EQ will surround themselves with a similar leadership team to create a superior culture in which individuals thrive, grow and develop while solving the aforementioned complex/impossible-seeming problems. Brilliant jerks exist, but are neither necessary nor sufficient for success as so much of what we do to build businesses is based on empathetic human-to-human relationships. A leader who lacks self awareness, cannot read the room, adjust tone or messaging based on who he/she is talking to, understand how his/her actions affect others, or how to recognize & manage emotions will typically not succeed in the long run and make everyone’s life miserable in the process.  


Look for leaders who have presence, who are intrinsically motivated by the mission and in turn exude a special kind of energy that is able to motivate others. As an employee, you’re generally being asked to sacrifice today for greater upside later while working long hours for many years to get there. Leadership teams who can make you feel the mission in your very being & continuously reinforce it are the ones to stay with.

Other qualities like prior experience and track record, subject matter expertise, and personal network, are important and can be instrumental in the success of the business, but not necessarily the culture within the organization.

While it may be impossible to vet all of this during an interview process, notice signs that indicate what the startup’s culture, mission alignment, and people are like - Do you interview with the senior leadership team? Do they address your questions and respect your diligence? Are they attentive and do you feel positive energy during the interview? Is there a thoughtful interview process in place? Can they explain what success looks like for your role? 

Once you’ve determined a senior leadership team you can trust, there is an even more important person you need to evaluate, your manager.  Next time!

Thursday, August 11, 2022

Evaluating a Company to Join, Culture: Mission & Values

If you’ve been trying to break Into Health Tech (or the start up world in general), hopefully you’ve been so productive that you have a list of companies you’d like to find a way to join.  So how do you evaluate a start-up?  

Taking a job is a prospective investment of your future time for a combination of daily experience: learning & doing, and financial rewards for success. Contrast this with monetary investments, which represent the past commitment of time.  For some reason or another, we seem to be much pickier at avoiding losses than seeking gains.  

I have come to strongly emphasize how my time is spent because “how we spend our days, is of course, how we spend our lives.”  Before we get into specifics of the role and title, let’s look at how you might evaluate a company as a whole, starting with it’s Culture.

The culture of an organization is a product of the mission, values, people (with heavy emphasis on senior leadership) that determines how a company is going to choose to solve problems.  It is said that Culture eats Strategy for lunch, so you better pay attention.  The culture created by company leadership, often the founding leadership, will determine the bounds of your experience– how each day will unfold, what is acceptable vs. forbidden, how you celebrate the highs and your experience during the lows.  

Here is one of the many, many great examples of culture at Iora Health.  While building the amazing Culinary Extra Clinic (CEC) in Las Vegas, Iora secured an apartment to ease the weekly commute from Boston (this all made sense at the time).  On the eve of my final trip to provide patient care and attend amazing farewell parties, my impatient son decided to come out early.  The entire company rallied around my family and CEC, covering patients, hopping on flights, missing spousal birthdays, inventing reverse telemedicine, etc.  The ever unflappable Rushika, Iora’s Co-founder, CEO and my Vegas roommate, came to visit us at the hospital and requested a duffel bag so that he could pack up my end of the apartment and bring my stuff home.  This time is only one of the many acts of kindness that defined Iora’s culture– empathy for each other especially in the hard times.  May each of you be as lucky as we were to create and work in such a wonderful place. 

Mission & Values
The mission of the company– what it sets out to do and why, combined with its values, how it chooses to behave in pursuit of that mission– are ultimately the most important thing in evaluating a company to join.  The reason is, these are the least likely to change over any period of time, so it is best to be inspired and in agreement with them up front.  Everything else– leadership teams, business models, products, markets, may change over time and each change will impact the mission, but in general the conditions and decisions made at the beginning tend to be very sticky.  Remember that later when we talk about stage later on.  

Mission alignment carries you through the hard days and directs you on the easy days.  Mission conflict will make you a very annoying member of any team, just go do something else. Values alignment grows you as a person while generating skill, confidence and calm.  Values misalignment creates irreducible friction that will spill over into every area of your life as you try to avoid it.  

Understanding the true mission and values of a company is challenging because a company may not know itself (this is bad). First, read any materials the company has published.  Second, ask!  Ask your interviewers, employees you meet, investors if you can about the mission and values and look for harmony or disharmony.  A company that says one thing and does another is a painful place to work, you can expect chaos and disappointment.  Spend time with the links above to learn more.  Needless to say, a company that lives its own mission and values that happen to match your own is a company you can stay at pretty much forever. 

Next time we will round out Culture with a look at the People that matter most inside an organization.

Thursday, July 28, 2022

How to Break into Health Tech

Following last week’s tactical career post, A Networking Email that Works, here is a method to crack into the Health Tech/Service Innovation startup world. I assume this would work in other start-up heavy fields, but cannot confirm. 

The startup world can be daunting, especially for those used to larger organizations and/or academia.  The risks are greater, the rewards are supposed to be greater as well, but the truth is, if you really, really want to change health care, start ups seem to be the best place to do it.  One strong word of advice on risk– the best way to deal with career risk is cash.  I highly recommend you have at least 6 months of full living expenses (you budget, don’t you?!?) before joining a high risk company.  Otherwise every ebb and flow will send you careening in unhealthy ways.  You read into every meeting to see if your family is going to starve, and that makes it hard to change the world. Ok, if I haven’t shaken you yet…

Cracking into the world of startups is a networking game.  As an academic physician (the role most likely to ask for advice in this scenario) you are both too expensive and know almost nothing useful to a startup.  That said, we clearly need doctors in digital health.  If you are not a doctor, the odds are that you know more and cost a little less, but the same patterns hold true.  

There are tons of digital health companies created and dying every day. Any database is out of date and so you need to create it in real time.  Fortunately, the journey is helpful.  

Step 1: Check out the portfolio page of high quality health care Venture Capitalists (VCs).  

VCs examples that I like from past positive experience are:

There are others, feel free to go wild, this is just a starting point.

Now, look through EVERY COMPANY on the Healthcare Portfolio page.  Pay attention to the ones that seem interesting to you and discard the rest.  I am a deeply intuitive decision maker, so I just go with my first instinct.  You do you. 

Step 2: Check out the Portfolio Company websites.  

You are looking for 3 things in priority order to pull you further:

  1. Company Mission including population served

  2. Leadership team background

  3. Open Roles page

The goal here is to find a company that speaks to you enough to reach out in Step 5.  Don't worry if there isn't an opening, reach out if you like the company as you never know what will happen. In a subsequent post we can go into how to evaluate a start up you’d consider joining (hint: think like an investor).

Step 3: Find out the other funders of companies you like.

Sometimes this information is on the company site, sometimes it is on Pitchbook or Crunchbase.  This lets you build a database, see who knows whom, and find the few companies or investors on which to target.

Step 4: Repeat until you have 5-10 companies you like, or run out of time or energy. 

Step 5: Reach out through your network

This one can be a bit tricky, but send A Networking Email that Works to anyone in your network that might get you closer to a company on your list.  LinkedIn is helpful.  If you don’t have anyone, send a cold email to the leadership team, what do you have to lose?  Alternatively, track down a VC (hint, the board members of the company who work for VC funds are usually the lead VC for that deal).  Remember you are going for an informational interview— to learn more about the company— not a job offer, so play it cool.  

Good luck!  Again, this took me 50-70 conversations before finding the right match for me, so be patient, polite and persistent.

Thursday, July 21, 2022

A Networking Email That Works

On the heels of the generalist series there has been some inbound requests from friends and colleagues for career advice.  The next few entries will outline a networking approach to gain entry and credibility when entering a new field.  First, here's the skeleton of the e-mail template that I’ve used to get in conversations with truly wonderful people that have had a profound impact on my career. 



WARM INTRODUCTION NAME suggested we should meet because of REASON YOU ARE GREAT.  I am QUICK BACKGROUND and looking to advance in DESIRED FIELD.  Would you be willing to spend 30 minutes with me to share your story: what you do and how you got there?

Thank you so much for considering,



That’s it, works almost all the time.  Now let’s break it down part by part to understand what is included and what is intentionally excluded.


Warm introduction

This one is a challenge starting out but gets easier over time.  A warm introduction, a reference from someone else in your mutual network, is crucial to get this person’s attention and ensure your legitimacy.  Additionally, this applies very mild social pressure so that they do not ignore you.  No one wants a colleague to follow up with “why didn’t you respond to so and so!?” and remember, the utilization and expansion of a network grows its value.

What if you don’t know anyone?  With LinkedIn and other social media, it is easier than ever to understand who you know and who they know. If you are persistent and pleasant, these conversations can start almost anywhere and chain you to almost anyone you’d like to meet.  A word of caution, never fake an introduction if you don’t have one.  It is dishonest, unethical, and easily disproved.  Expect the recipient to check with the referrer before responding. 


Reason you are great:

A quick summary of your understanding of their expertise.  Flattery never hurts, especially powerful people.  Examples include: “your success in health tech.”  The important part of this sentence is that it is about their greatness, NOT YOUR NEEDS.  By being self-centered you give your recipient a guilt-free excuse to not do something nice for you.


Quick background/Desired Field:

Self-explanatory, keep it brief.  “I am a medical student looking to get into entrepreneurship SO THAT I can improve care in this country.”  This establishes your value and interest without spending too long on yourself. Do not inquire about specific roles, jobs, internships, etc. for reasons that will become clear in a moment. 


Your Story:

This is the hook of this email.  Most messages contain requests for favors which, other than being rude, fail two basic tests of action: First, there may be no makeable deal.  If you ask for a job and there is no job, then the answer is at best an apologetic “no” and the close of communication. Second, you’ve failed to appeal to the recipient’s self-interest in your request. However, due to the Ben Franklin Effect you still want to ask for something, and this is where the story idea comes through.  One of the best pieces of advice that I ever received was to listen to everyone’s life story, decide which ones appeal to you most, and then spend as much time with those people as possible.  It is an ingenuous, genuine method of learning about others and one’s self. Furthermore, everyone loves to share their version of their story!  They are rarely asked (or not often enough!).  You appeal to your recipient’s desire to teach, share and contribute which is a very powerful force.  Additionally, you will begin to see patterns of action and sequences of events and the incredible role of capitalizing on luck that plays into success.  By limiting it to 30 min you are minimizing the burden.

Now, what happens if they agree?  Easy—schedule whatever time they give you. Early, late, weekends, whatever.  Again, this is about them, not you, so make it work however you can.  Someone once asked me for a favor and then complained that the availability I offered them THE NEXT DAY was “too early in the morning for them” (7am local time!!).  Needless to say, that was not a productive relationship.  Also, block at least a 30 minute post call buffer in case it runs long (which is always good), for you to write a thank you email, consolidate your notes, and predictably, send the emails to the next set of individuals in the chain recommended by your recipient.


So now that you have the meeting scheduled, what are the possible outcomes?  Best case scenario- you find a mutual match, you get along well, the story is thrilling and a wonderful relationship begins.  This is extremely rare, but don’t worry, you only need one or a few of these relationships in your whole career.  Rarely, there is no magic, you don’t get along and the call ends in a dead end. Oh well, thank you note away! The most likely outcome is that your new colleague will suggest 1-5 people to whom you should speak next.  When I started this journey I was lucky enough to get 10 recommendations (!!) from an early meeting which changed the course of my career.  If they offer contact information, great, if not don’t ask.  Don’t make them do work, you can figure out an email address or LinkedIn profile.  Do ask if you can use their name as WARM INTRODUCTION.  And on and on you go! 

You may need 5 conversations, you may need 75 (I did), but persist in this method and you will develop lifelong, mutually productive relationships with mentors and colleagues. Good luck!

Thursday, July 14, 2022

Career Path for the Generalist, Part 3: The Integrator

I hope you’ve enjoyed the first two parts of the Generalist Career Path!  I’ve gotten great feedback which motivates me to continue writing. A word about part 3: read the links. It is worth getting familiar with the concepts as I attempt to create my own unified theory. I’ve also revised Part 2: Interpreter if you’d like to quickly re-read. 

If the Commando gets shit done across specialty domains, while the Interpreter builds empathetic relationships across specialists within domains, then the Integrator evolves from the previous phases to create lasting value by… integrating across domains. Maybe this is what you have secretly thought you should be doing: designing solutions: organizations, technology, services and products that combine specialties to create something new from the composite parts.  Perhaps you’ve even been frustrated by specialist bosses (twos) who cannot see what you can see.  Remember, your value is not the depth of your skill but rather the breadth of your skill.  As such, you are uniquely positioned to see what others cannot, similar to the concept of Chance III.  

Charlie Munger, perhaps the most successful generalist, put it best:

“each discipline entwines with, and in the process strengthens, every other. From each discipline the thoughtful person draws significant mental models, the key ideas that combine to produce a cohesive understanding. Those who cultivate this broad view are well on their way to achieving worldly wisdom.” --Investing: The Last Liberal Art by Robert Hagstrom

And that is the role of the Integrator–to lead organizations with wisdom to solve really, really hard problems.  As your organization grows and succeeds, the problems you face will traverse the Cynefin framework into complexity and chaos.  Setting up payroll is complicated, but it is a solved problem requiring one or two functions.  Similarly for getting everyone laptops, launching  an email client or ordering furniture.  As your organization grows, it slows, in part because you run out of obvious, comfortable, single functional problems. 

To solve this coordination challenge, bureaucracy starts to emerge in the form of project plans, timelines and the dreaded “accountable person” to ensure work across functions and this naturally ends in failure.  Why?  Simply– complex work requires cross-functional nuance, which is not the same thing as merely combining single functions in a meeting.  Furthermore, the choice “accountable individual” exposes your organization to both the Sartre problem and Conway’s Law in that the solution space is predetermined by the choice of designee.  Software teams tend to solve problems with software, compliance teams with policies, and operators with procedures.  Whichever specialist you choose will terminally bias the outcome.  What the organization requires is someone who understands what everybody does to combine them in novel ways to solve novel problems: the Integrator!

A successful Integrator requires legitimate power by virtue of a senior leadership position because the greatest challenges will be your specialist peer leaders who are looking for control over their resources, certainty and predictability (and often fallaciously desiring full utilization) that is inconsistent with creation and novel problem-solving.  Empathy is important here but so is urgency, you have to bring your peers along in a Goldilocks fashion, which is a challenge I continue to struggle with as a leader.

If you can pull it off, it is amazing what your organization can accomplish.  Work is clear as it is made visible, work in progress drops and with it all the fires start to go out.  No more draining weekly update meetings with no time to do the work. Incredibly rare evening and weekend emergency meetings.  Work gets done faster as you do less of it at once because teams work together instead of in a never ending arms race against one another.  The sense of calm, controlled progress is intoxicating and sounds too good to be true.  However, once you’ve been on the other side you cannot imagine going back. 

And this is about as far as I’ve gotten in 40 years so it is as far as I can take you now.  Perhaps I will write future parts as I learn them. 

-- Special thanks to Marie Castelli for sharing the HBR Integrator article!