5 tips to coach and mentor future leaders


While this article by Lisa Jasper on Insperity’s blog is focused on tips for coaching and mentoring future leaders, these tips are certainly applicable to founders of startups.

Her key point is important for any organization: Talent development requires a serious commitment of both time and resources.

Here are the 5 tips she recommends, read her post for details on each tip:

  1. Identifying leadership
  2. Begin a conversation
  3. Develop through experiential learning (most applicable to mature companies)
  4. Build in both coaching and mentoring
  5. Don’t forget the soft skills

Lisa makes a distinction between mentoring and coaching:

Mentoring differs from coaching in that it generally occurs over a longer period of time and focuses on developing the individual holistically for the future. Coaching normally focuses on the short-term. Coaching helps an individual overcome a specific, current issue or performance challenge.  Used together, mentoring and coaching strengthen and mature future leaders.

Insperity is an HR consulting firm. There are interesting overlaps between the mentoring that goes in inside companies and the mentoring of founders through colleges and university entrepreneurship programs and in incubators and accelerators

To Succeed at Startups and Innovation, You Need Great Mentors

wes stringfellow

Wes Stringfellows’ post on the TechStars blog is the strongest endorsement I’ve ever seen of the value of mentorship.

He says:

You can boil Techstars’ track record down to one thing: mentorship.

Techstars has mastered the art of mentoring. Without it, most startups – and many innovation efforts – fail.

Here’s what amazes me: the proven value of mentoring is right out in the open, yet the vast majority of innovation initiatives fail to leverage it. Mentoring is literally the secret sauce of every accelerator.

He backs up these very strong statements with data:

Endeavor Insight studied thousands of startups and interviewed nearly 700 founders, and they validated the powerful role of mentoring. 33 percent of founders who were mentored by successful entrepreneurs went on to become top performers.


Wes lists three reasons why mentorship works in his experience working with TechStars. Read his post to get the details:

  1. Entrepreneurs and Innovators were willing to accept help
  2. Experts were willing to offer help
  3. Positive ways to say “no”

He concludes with this advice, which founders ignore at their peril!

I feel so strongly about this that my advice is that you are crazy to launch an internal innovation effort – or a startup – without first understanding how you will gain access to mentors. Not just one or two, but multiple mentors with expertise in the numerous specialties you will need master to succeed.

West Stringfellow is the Vice President of Internal Innovation and Operations at Target Corporation. West’s career has focused on driving innovation at scale. He has had executive-level innovation and product management roles at Target, PayPal, VISA, Rosetta Stone and Bigcommerce. @westringfellow

Always the more beautiful answer/who asks the more beautiful question


I’ve been a devotee of the Socratic method for many years and have found it especially useful in mentoring founders. So I was excited to find what appeared to be an entire book about the power of questioning: A More Beautiful Question by Warren Berger. The good news is that the first 75 pages or so do focus on the power of the question and why it’s so important in our time of accelerating technological change and complexity. Unfortunately the rest of the book degenerates into the typical business book pastiche of a zillion quotes from people you’ve never heard of and endless variations on the author’s main themes. What would have made a great long form article on Medium, The New Yorker or Vanity Fair has gotten inflated into an entire book. That being said, I still recommend the book, especially, for educators, as Warren Berger focuses a great deal of his attention on what’s wrong with today’s (and yesterday’s) education system: a focus on memorizing and regurgitating facts as opposed to learning how to ask important questions. I found myself underlining sentences multiple times per page – there are great quotes and stories about the power of the question. (Do yourself a favor and buy the paperback or the Kindle edition and save yourself some money.)

One story which I particularly like, though it may well be apocryphal, is the story about Einstein. He said that if he had an hour to solve a problem and his life depended on it, he’d spend the first fifty-five minutes making sure he was answering the right question.

Clayton Christiansen observes that questioning is seen as “inefficient” by many business leaders, who are so anxious to act, to do, that they often feel like they don’t have the time to question just what it is they are doing. I’ve found this especially true of founders with their bias for action and strong sense of urgency.

Berger offers a powerful definition of a beautiful question:

An ambitious, yet actionable question that can begin to shift the way we perceive or think about something – and that might serve as a catalyst to bring about change.

Another important insight that resonated especially well with me was that “questioning often has an inverse relationship to expertise – such that within their own subject areas, experts are apt to become poor questioners. Frank Lloyd Wright put it well when he remarked that an expert is someone who has “stopped thinking because he knows.”

Most people are reluctant to ask question for two reasons: one, that they may appear stupid, or more precisely ignorant;  and two, that they may appear to be questioning authority, which might endanger their career prospects. When I unexpectedly found myself in the personal software industry in 1980 with only a light hobbyist knowledge of computing and surrounded by MIT educated software engineers, I quickly learned that if I didn’t ask questions I would never learn what I needed to know. And in fact no one considered me ignorant for asking questions and sometimes my non-expert questions even catalyzed discussions amongst the expert engineers.

My most powerful takeaway from Berger’s book, the insight that is most relevant to mentoring founders, is that it is not the questions I ask the founders that are so important, but that I help them learn the power of asking questions themselves, of their colleagues, the world around them and themselves. As Leon Bernstein, president of Bard College, is quoted on the power of questioning: “… the ability to question not only other people’s views, but one’s own assumptions.”

As Jay Ito, head of MIT’s Media Lab said, “you don’t learn unless you question.” And as I’ve posted before, startups are learning machines – experimental labs where the founder forms a hypothesis, designs an experiments to gather data to test the hypothesis, and then modifies their thinking based on the results of their experiment. Iterate until true.

I could go on quoting salient sections of Berger’s book and quotes from the many people he has spoken to or read about, instead I recommend you buy the book and make these discoveries for yourself. And perhaps, unlike me, you may even find the latter chapters as valuable as the first.

Y-Combinator launches Startup School MOOC


tree_white-fd2b43a5fe542d662d7ceea9a9a2a3def99e00f8f3bd32bf27634298b383cb92Y-Combinator, the massively successful accelerator that has invested in over 1,500 companies including unicorns like DropBox and AirBnB, has now launched a MOOC, (Massive Open Online Course) known as Startup School.

We believe the barrier to entry for people to start a startup is still too high. We want to make it easier for people to start a company, regardless of who or where you are, so we’re starting by sharing what we’ve learned, through Startup School.

Startup School is a free 10-week massively open online course (MOOC). The course will begin on April 5th, 2017. Lectures will be posted here weekly.

Registration will close by March 27th, 2017 Pacific Time. So better sign up now!

There a helpful FAQ that tells you all you need to know, for example:

How many hours should I expect to put into this?

For Startup Founder Track (people who’ve already started working on a startup):

There is a minimum commitment of 3 hours a week: one hour of lecture, one hour of class office hours and one hour of group office hours. How much additional time you decide to work on your company and engage with your advisor and the community is entirely up to you.

For spectators:

Just two hours per week (lectures and class office hours).

I’ve signed up myself, as I’d like to turn my part time mentoring into a startup. I’ve watched several of the Y-Combinator videos on YouTube and have learned a great deal from the interviews with famous founders and investors, like Mark Zuckerberg , Drew Henson, and Mark Andreessen.  I’ve never signed up for a MOOC before, but the idea has fascinated me for some time. So as I’ve discovered I’m not getting any younger, the time to try one out is now!

The accuracy of information about startups degrades exponentially over time


One of the lessons I’ve learned over years of mentoring is that everything you can find out about a startup or founder is out of date! Virtually all mentoring programs require applications from founders. I used to read these applications assiduously in preparation for the mentoring meeting, only to find that the company I was mentoring bore no resemblance to the company that applied for mentorship. Why is that? Well most of those applications were done weeks if not months before the meeting and the rate of change in a startup is not linear, it’s exponential. And the earlier the stage of the startup, the faster the rate of change.

The same goes for web sites. Most founders are far too busy to keep their web site up to date – assuming they even have one. And even if they have the time, given that many founders are anxious about having their ideas stolen, web sites present only the public face of the company – the rest of the organism kept hidden from public view.

So mentorship applications, web sites, and executive summaries all degrade rapidly with time and in fact often become misleading. Generally the younger the company the more rapid the rate of change. So while I have had a hard time breaking the habit of inhaling any information I can find about my prospective mentee, I’ve learned to start the relationship at square zero.

Many founders come to their first mentor meeting with a pitch deck that is more up to date than their other documents – but even pitch desks are not current.

So I’ve found the best way to start a mentoring meeting is with introductions. Not only does this give me useful information on the founder’s background, but also enables me to evaluate how well they can present without the aid of a slide deck. And it also gives me a chance to introduce myself and highlight what elements of my experience may be most relevant to the founder’s venture. This is also a good time to explain that mentors, unlike venture capitalists, strictly adhere to the confidential non-disclosure agreements they have signed with the parent organization.

Once we are past the introductions the next step is simple: “Tell me your story.” Whether that story is focused on starting a company or creating a product is a “tell” – are they in it for the long term, the years it may take to build a successful company? or are they looking for a quick hit? Build an app or service and sell it ASAP. There’s no right answer, but the founders should be clear – and in agreement – about the objective of their venture.

Even when a founder tells their story with a deck you need to be careful to check – is this deck up to date? When was it prepared? And was it done for an investor, for a business plan competition, or just for the mentor meeting (a rare occurrence)?

The bottom line is when reviewing a founder’s materials – application, web site, or pitch deck – or even hearing their story in real time, don’t assume the information is always up to date or accurate.  The most common element that changes is the status of founders. It’s always advisable to ask, “is he or she full time with the company?” Often, especially in the case of students, the answer is no – they are also pursuing a degree. And even if they aren’t a student, one or more founders may have a “day job” to pay the rent. Or their joining the company may be conditional on a Series A round or some other event.

You can’t successfully mentor a founder if you are relying on out of date, inaccurate information. If you’re in doubt about any element of their pitch – business model, status of the founders,  or their perceived competition – ask!

The founder’s story is the foundation on which you build your mentoring relationship, so make sure you have a solid foundation from the start.

And one piece of advice you can give your mentees is that when they are doing a competitive analysis don’t rely on web sites or press releases – better information might be found on social media or best yet, via that old standby, the grapevine.

What makes a good mentor protégé relationship


Prajakt Raut, a seasoned entrepreneur, has an excellent article on on the relationship between mentors and mentees, whom he calls “protégés”

Here’s the definition of protégé:


a person who is guided and supported by an older and more experienced or influential person: he was an aide and protégé of the former Tennessee senator.

As you can see it’s not very different from mentee:

mentee |menˈtē|


a person who is advised, trained, or counseled by a mentor.

Prajakt Raut has a lot to say and I recommend you read the entire article, whether you are a founder or a mentor. But here’s a few highlights:

A good mentor-protégé relationship can be game-changing for a startup, and therefore it is important that both – the mentor and the protege – understand how they can make the engagement meaningful, productive, rewarding and fulfilling.

Apart from strategy and help in decision making, a mentor could also help in the following areas:

  • Helping create a business case and business plan
  • Helping with warm introductions
  • Providing support during tough times
  • Helping take tough calls
  • Interviewing senior employees

And he has an excellent list of common mistakes protégés can avoid including:

  • Most importantly: Do not get a mentor just to hear more validation of your ideas and assumptions. Get a mentor only if you are willing to be challenged on your ideas and plans. (I notice some entrepreneurs just seek reaffirmation of their beliefs, and if that is not the case, they can be quite dismissive of the mentor).

If you can’t spare the time to read this entire article watch his video, which is a good summary in less than 60 seconds!

To get the right answer you need to ask the right question


When it comes to mentoring I’m a big proponent of asking questions of founders, as I posted in Ask don’t tell.

But Elon Musk goes further – he’s a proponent of founders asking themselves questions, the right questions.

The article Elon Musk on the 1 Creative Skill Every Founder Needs Now by Lisa Calhoun is a recommended read for both founders and mentors.

Musk believes, “A lot of times the question is harder than the answer. If you can properly phrase the question, then the answer is the easy part.”

Asking the right questions is a skill that can be learned, according to Warren Berger, bestselling author of A More Beautiful Question.


Berger says when he mentors that, “Oftentimes there may not be a right question. You know you’re asking a good question when you get sort of a rise out of people.

I agree with Berger, but I can define what I mean by a “rise our of people”. Oftentimes founders at mentoring meetings start off leaning back in their chairs. I know when I’ve asked a good question when they lean forward, elbows on the table. Some entrepreneurs even start meetings as “shoe gazers”. But again, if you ask a good question their heads snap up and a light goes on in their eyes. So non-verbal communications are a good way to tell if you’ve gotten a rise out of founders by asking a good question, if not necessarily the right question.

Musk says “To the degree we better understand the universe, then we know which questions to ask.” He gives a great example:

So Musk asked another question–why are rockets so expensive? “I came to the conclusion that there was really no good reason for rockets to cost so much, and they could be less . . . a lot less. If one could make them reusable, like planes, the cost of space travel would drop dramatically. The cost of the fuel was .2 to .5 percent of the cost of the rocket, kind of like the plane.” In fact, “Nobody had been able to make a reasonable rocket work–and I thought, if we can do that, that would be a breakthrough for space travel.” SpaceX was born.

To the degree we better understand the founder’s idea and personal aspirations in pursuing that idea we then know which questions to ask.

Questioning the status quo by asking Why? can be the first step in starting a new company. But as Warren Berger says of asking the right question:

That’s a good starting point.” Then, he says, getting your question in the world for feedback is the next step. The results of gaining feedback on the question, possibly through a demo or other minimum viable product, will help you understand if the question is ‘the right question’–or not.

Jay Ito, head of MIT’s Media Lab says:

“It’s a time of exponential change, so things are different every day. The old model of learning–that you do a lot of it when you’re young and then become an adult who doesn’t learn as much–that just doesn’t work as a productive way of living now. You have to learn new things all the time. And you learn by being curious and by questioning.”

So founder or mentor, learn to ask the right questions, of yourselves and of your mentees. You’ll learn a lot by so doing.