Mentors ask questions to help founders find answers

8 questions

I learned how to use the Socratic method in management from Wayne Oler, then president of Addison-Wesley Publishing Company, where I was General Manager of the Educational Software Division. Wayne rarely made a statement. Even if you were clearly in the wrong he wouldn’t say so. For example, I remember being in one meeting where an executive used the term “budget” when he clearly mean “forecast.” Instead of correcting him Wayne sort of cocked his head and said, “Do you mean “budget” or do you mean “forecast”? The executive quickly corrected himself and the meeting moved on. Coming from a very hypercritical family this was a real lesson for me. Don’t point out people’s errors. Help them discover them. And maybe they aren’t even errors! By asking questions you may find out you were operating under the wrong assumption and the other person was in fact correct. And mentoring is about being right, it’s about helping the entrepreneur get to the answer that’s right for them and their venture.

And mentoring isn’t about right or wrong, it’s about learning. And the best way to learn is to ask questions. I try to model that behavior with my mentees. I was pleased to see the articleThe Best Mentors Ask These 8 Questions – an essential part of being a good mentor is asking the right questions by Gwen Moran in Fast Company.  These questions come from Lisa Z. Fain, CEO of The Center for Mentoring Excellence, a mentoring consultancy and coaching organization. “For mentors, the most important thing, really, is to ask questions, to be this guide on the side, rather than the sage on the stage,” she says.  Here are eight questions good mentors ask according to her. Per usual I’ll list the question but add my own comments.


This question is ok, and perhaps it’s intentionally vague, but I prefer a question more like, “How will you measure success?” or “How will you know when you are successful?” Measurement of success is important to founders in at least three different ways: in their own company, in strategic alliances, and with customers. Teaching them to understand what success means and how you measure it by asking this question as a mentor helps founders learn this technique to use themselves, including how they will mentor their staff.


I always tell founders that we can’t help them unless we know where trying to get to. I use the old saying, “If you don’t know where you are going, any road will take you there.” This is a very important question for ventures with more than one founder. The outcomes, whether it’s going public, getting acquired, or creating a lifestyle business must be congruent amongst the founders or conflicts will arise from the get-go. It is surprising how little thought early stage founders give to this. See my post Product or Company? for a bit more on this subject. Whether you want to build an app and sell it ASAP or try to build a company like IBM that lasts for 100 years, doesn’t matter. And it doesn’t matter if you decide to change that goal. What matters is complete alignment of the organization behind the vision and the goal. That’s job one for a CEO.


Business plans used to ask for 5-year projections but I doubt that many do today. Things are just moving too fast. Five years ago a tiny fraction of entrepreneurs even knew what a blockchain was. Now it’s hard to find a startup that doesn’t include blockchain in their product plans. So asking what you want to be different in five years may stimulate the founder to think about their aspirations, but perhaps it’s the very pragmatic stance of MIT’s Venture Mentoring Service where I’ve volunteered for going on 9 years, but I find three years out to be a more reasonable time frame.


I have a somewhat different way of asking this question, “What’s keeping you up at night?” Either way it is important for mentors to get good answers to this question so that we can use the very limited time we have – a typical meeting is 90 minutes and we might have one or two meetings a month at most – to prioritize the areas where we try to provide advice, feedback, and guidance.


I’ve never heard this question asked! I think it would steal time away from asking the above question. But I just might try it to see what kinds of answers it elicits. As you’ll see if you read the original article, this question seems more appropriate for mentoring someone inside a corporation rather than a founder of a startup.


I like to go beyond this question to getting the founder to list the pros and cons of each option. So for example, if they are having difficulty gaining customers fast enough, one option might be to lower the price. This might have the pros of getting more customers to buy the product but the con of reducing cash flow and profitability. One can get more sophisticated still in asking the mentee to work through the repercussions of each option by developing decision trees. See my postHow do you make decisions?


This one’s right out of a Rogerian therapists playbook! And that’s a playbook worth stealing from. Mentors aren’t therapists, but we do need empathy with our founders and there are other similarities. When there’s more than one founder in the mentoring session this question can be addressed to a different founder to see how their perspectives may differ.


This is a good way to get to know someone and also a way to suggest books or articles that we might want to recommend to a founder. I haven’t used this one, but again, it’s a question I might try if I can fit it into our time slot.

Questions tend to get people to open up, to reflect, to think. Statements can often make people feel defensive talked down or come across as too didactic and to close down. On the other hand sometimes a statement is the shortest route to providing good advice. For example, a founder starting a service that provides health care options to the elderly should definitely look in to liability insurance. You don’t need to have a conversation or discussion on something like that. But of course you can always phrase a statement as a question, “Have you looked into acquiring liability insurance yet?”

And here’s one question an experienced mentor always asks during the session, “Are we bring helpful?” Mentors need feedback too!

Get it in writing!


Consumed by litigation, 600 lb gorillas founders Chris and Paula White have stopped making ice-cream sandwiches and cookie dough.

My father had a bunch of saying which have stuck with me for years. Whenever something bad would happen he’d say, “Well it could always be worse.” Whenever I talked about something good happening in the future he’d reply, “Don’t count your chickens before they hatch.” And “If it seems too good to be true it probably isn’t.” A couple of incidents in the news recently reminded me of another one of his favorites whenever I talked to him about business that involved another party’s commitment to making something happen: “Get it in writing!”

The big news item, at least to pro football fans like me, was when Josh McDaniels, the long time offensive coordinator for the New England Patriots, seemingly had left the Pats to join the Indianapolis Colts as head coach. By itself this news didn’t surprise anyone as McDaniels had entertained offers for head coaching positions before.The big surprise to everyone, most especially to the Colts was when Josh announced he had changed his mind and would stay with the Patriots! And this happened the day before Chris Ballard, the General Manager of the Colts, had scheduled a public event to announce Josh as their new Head Coach. It turns out that Josh had never signed the contract the Colts had offered to him, so they had no recourse! Chris, next time, get it in writing!

The other incident was in a Boston Globe article by Janelle Ramos the other day, How the partnership between 600 lb Gorillas and Mister Cookie Face crumbled. It’s a rather complicated story about how two founders were victimized by the failure of a much larger supplier to deliver ice cream that met their standards, which would have allowed them to cut costs, aside from the fact that they received except for the fact that they got tons of complaints from customers that the new ice cream was  “tasteless,” “watery,” “awful,” and “kind of icky-tasting,”

Turns out that the entrepreneurs had only an oral agreement with the supplier! Long story short, they are now embroiled in a legal battle: Over the last two years since filing suit, the Whites have been consumed by the litigation and have stopped making ice-cream sandwiches and cookie dough.

So there are not one but three morals to this story: one, despite the fact that oral agreements may be binding in some states, get it in writing! Second, don’t rely on a single supplier that is critical to your business! And finally, if you are a little guy be aware that getting into a legal fight with a big guy means you will lose. They have more resources than you do and will tie you up in court while your business withers on the vine. As one of the founder’s lamented:

“These larger businesses really don’t care, and they think they can get away with whatever they’re doing to a little guy like me,” said Chris. “We gave up decent careers and took a chance on something. This is our livelihood, and we need to get it right. We can’t sell a bad product at a premium price.”



Conventional wisdom about pitch decks that’s best ignored


There are probably more articles about how to create a pitch deck than there are venture capitalists. So rather than reiterate the conventional wisdom I’m just going to touch on a few elements of the conventional wisdom that you are best off ignoring.

  1. Use 10 slides – not more! I first ran across this one from Guy Kawasaki in his book The Art of the Startup.  (This book is so old he focuses on the size of the text in your bullet points! You do know that everyone hates bullet points and they are to be avoided at all costs!) The problem with this idea is what is important is how much time you’ll have to tell your story. And that is what you are doing telling a story: there’s a beginning – your origin story, how you got the idea for the business; the middle, the problem you are solving and the customers you are targeting; and the ending, how you will make money and build a company of lasting value. So you could do this in three slides, or maybe 15. The important thing is not how many slides you present but that you present one and only one idea per slide. The rule of 10 slides often results in founders jamming so much stuff into their slides the message gets lost in the noise. Each slide needs to be impactful and reinforce, not just repeat, what you are saying. Think of the illustrations in a children’s book – your slides need to illustrate your message, and be memorable.
  2. Spell out how your business will perform for the next 5 years. This is old school thinking. Back in the days we wrote 20 page business plans with half a dozen pages of financials. In today’s rapidly accelerating rate of change anything past three years is pure fiction. Project three years of your business, with maximum detail in year one. Once you are actually up and running you can keep up a rolling 3-year projection, but you won’t get to year one by trying to con investors that you can project the future 5 years out! If you could, forget about being a founder and become a stock picker!
  3. Investors need to know your exit strategy. When Dan Gregory, then managing director of Greylock was asked if he wanted to know our exit strategy he replied, “Your job is to build a great company. Do that and the exit strategy will take care of itself. Don’t, and the exit strategy will … take care of itself.” Angels will often insist on knowing your exit strategy, but VCs are more sophisticated. You want patient capital. VC funds run 10 years, so you should plan on returning capital to your investors in 5 to 7 years. But how you’ll do that will remain to be seen. Focus on creating value everyday and you’ll have the right options when the time comes.
  4. Make sure you include a slide of financial projections.  And make sure it’s got the hockey stick curve showing the investors how they will make 10x their investment too!  Rather than crystal-balling future revenues, spend a lot of time understanding the key metrics of your business: the size of the total addressable market, its growth rate, you ARPU (Average Revenue Per User), your cost of customer acquisition, customer churn rate, and the lifetime value of a customer. Your closing slide shouldn’t be the Excel hockey stick that any first year MBA can crank out but a simple reiteration of the why investors need to invest in your venture, now: because you have a world-class team solving a major problem in a huge and growing market!

Keep in mind that a pitch deck is an unnecessary evil.  You are far better off demoing a knock ’em out of their seats prototype then having a discussion with the investors that addresses what they want to know, rather than subjecting them to death by PowerPoint. See my post Why a prototype is worth 1,000 pitch decks.

Finally read the article 12 KPIs you must know before pitching your startup by Phil Nadel, founder and managing director at Forefront Venture Partners. Your ability to knowledgeably discuss these 12 KPIs is far more important than any financial slide you can cook up with Excel or nowadays, Google Sheets. Keep in mind your goal in a meeting with investors is a meaningful conversation, not a canned presentation.

What I’ve learned from reviewing 20 applications for the MIT VMS Demo Day

As a mentor at MIT’s Venture Mentoring Service I was very fortunate to be given the opportunity to review 20 of the 50 applications that were submitted in the General category for Demo Day – probably because I’m a generalist! While all the information in these applications is confidential, I can share a few things I toke note of and provide some insight into how to become investor-ready.

  • Have a great team and toot their horn: From my experience founding four venture backed companies, raising multiple rounds of investment for those companies, plus attempting to raise capital for a few more, I’m confident in saying the most important element in being an investor-ready startup is having a great team. The biggest mistake founders make is not highlighting the experience and expertise of each team member that is relevant to their startup. And relevant is the key. Why will these team members help the venture become to successful? Too many applicants simply list names and titles, without listing either responsibilities or relevant experience. And my pet peeve is seeing COOs! There is no need for a COO (or a CFO) in an early stage company! There are only two jobs in a startup – making the product and selling it. COO’s and CFO’s do neither – very are just overhead!
  • Tell what you did, not what you are going to do! Too many applicants don’t show any evidence of customer engagement, traction or whatever term you want to give to customer discovery and development. You aren’t investor-ready until you can demonstrate customer engagement. At minimum you should have had two or three successful pilots and evidence you can convert a pilot into a paid customer. I’ve seen too many applicants without this evidence of traction, rather they say something like “we’ll have the beta done in two weeks!”  Focus on what you’ve accomplished that’s what you will be judged on, not what you plan to do, not that it isn’t important to provide a product roadmap.
  • Don’t ignore margins. For those relatively few companies that have revenue you need to provide some information about your gross margin. It’s ok if it’s small or even negative, so long as you present a sound plan with evidence to back it up that as you scale your margins will improve. No one expects a startup to be profitable right off the bat. In fact is a bad idea, as you should be investing in product, business, and customer development as an early stage company. How will you achieve economies of scale? Keep in mind: investment is for one thing – scaling up. if you aren’t ready to scale you aren’t investor-ready.
  • Be specific about your use of funds.  Use of funds should be broken into two categories. One, how will you spend the money? For example, We will hire two more software engineers at $100k each. And two, what will you achieve with that investment? For example, One engineer will develop our iOS version of the app and the other will develop the Android version; both will be ready inside of 6 months. Spending should be tied into reaching milestones. The clearer you can make your use of funds and what you will accomplish with those funds the more likely you are to receive an investment.
  • Raising friends and family funding is a plus. No one likes to go first and that includes investors and customers. Investors are always looking at how to de-risk an investment. If you have raised friends and family money that helps validate the business concept. Some investors like to see founders put in their own money. I don’t think that is necessary, but it is a plus.
  • It’s not just about the market it’s about growth. Many founders attempt to size their target market but forget to include it’s growth rate. For example, VR gaming is a small market today, so what’s important is supplying evidence that it will grow rapidly. And what are the market drivers? Investors don’t like to put money into a shrinking or stagnant market where competition results in a zero sum game.
  • Have a great video on your web site. If you are still in stealth mode password protect you video if necessary. But spending the time and money on a short – one to two minutes max, can be very effective in portraying your company. And videos have great passalong value, making them a good promotional tool.

The questions for applications for demo days and for acceptance into an incubator tend to vary. Don’t cut and paste your answers! Read the questions carefully and answer them clearly. Don’t act like a politician who replies to a question with “I’m so glad you asked me that!” and then goes off on a tangent unrelated to the question! If you are building your startup carefully and correctly you’ll have no trouble filling out these applications. But before you do, make sure you’re going to have a great demo! It doesn’t help to get accepted for a demo day if your demo isn’t really inspiring. Before you even apply attend several demo days and take note of what gets investor’s attention. And what does not.

Learning from failed startups


I’ve never sat down to list all of my startups, let alone what if anything I learned from them. But Vikram Joshi, co-founder and CTO at Pulsd did in his Forbes article Five Things I Learned From My Failed Startups. Per usual I will list each of what he calls “learnings” – which isn’t a word where I come from – and annotate them with my comments.

1. Do Not Go Solo

It was obvious my original idea for the Mainspring business was a failure – trying to create Microsoft Developers Network for developers of web sites and web applications was a non-starter as the web was soon flooded with this kind of information for free. We had even considered giving the many millions still left in our bank account back to the investors. I decided to leave to start a new company, Throughline. I made the mistake of basically going solo. Now I always recommend against it. Startups are hard enough for two or three co-founders, let alone one founder. Co-founders bring not only experience and expertise you may not have, but also perspective and their own personal networks. Don’t go solo! And if you can’t attract a co-founder there is probably a flaw in your business concept.

2. Do Something That You Are Really Passionate About

Again I agree totally with Mr. Joshi. One of my many startup ideas that was way too early was remote monitoring of diabetes patients. Not only was the technology not there, but I wasn’t passionate about helping diabetics. When I found that doctors really didn’t like diabetics – they tend to be very overweight, don’t follow their prescribed diets, don’t take their meds, etc. – I very quickly folded my tent as I thought my tech idea was cool, but I had no affinity for diabetics. Startups are a marathon, not a sprint, so if you are not totally passionate about helping your customers don’t even start.

3. Launch Beta Sooner Than You Think You Should

I learned this lesson the hard way with PopSleuth and Endorfyn. We spent way too much time and money before we launched Endorfyn – a mobile app to help fans find the latest works from their favorite artists. If we had launched a lot earlier – and frankly focused on customer development not product development – we would have found that the audience for this app was very small and that it would take gobs of money to find them and get them on the app.  You have to get engaged with the market even before you start coding – create some mockups and get them in front of your target audience.

4. Have A Balance When It Comes To Market Research

You may want to read my blog post Market research – what is it and why you need it. What you need to focus on is primary market research: get out of the office and talk with target customers, don’t sit at your desk using Google! But don’t neglect using Google to find your competitors, that’s where it’s really helpful. It surprises me how many founders neglect this step. In mentor meetings there’s often a mentor searching Google for competitors!

5. Do Not Ask For Funding Too Soon

With Mainspring we not only asked for funding too soon we got it! Eight million dollars for a business plan! It was far more money than we needed and way too soon – we hadn’t talked to a single prospective customer. Talking with friends and family about your startup idea is no substitute for talking with total strangers who won’t be biased in your favor. As the saying goes, first you have to nail it, then you can scale it. Investment capital is rocket fuel – it should be used to help you achieve escape velocity. Sweat equity and perhaps money from friends and family gets you onto the launch pad and ready to raise institutional capital. Recommended reading:  Nail It then Scale It: The Entrepreneur’s Guide to Creating and Managing Breakthrough Innovation by Nathan R.Furr and Paul Ahlstrom. 

The great thing is that it’s never been easier to start a company with hosting from AWS and distribution through the App Store and Google Play and billions of venture capital looking for the next great thing. But the bad news is too many would-be founders jump in with booth feet. Look before you leap! If I learned anything from my many failed startups it’s focus on customer discovery and development, not product development, not business development. You will still make mistakes but you won’t commit the cardinal sin of not knowing who your customer really is.

The driver behind auto-didactism


What do Steve Jobs, Bill Gates, and Mark Zuckerberg have in common? They all dropped out of college to start their companies – and never went back. And they all were/are

And if you, your founders, and your company are going to successful you all need to be or become autodidacts. Because the rate of change of what’s important to learn is so fast that even if you do graduate from college by the time you get around to framing your diploma your knowledge is obsolete. As I quoted Microsoft CEO Satya Nadella in the post Startups are learning machines, “We want to push to be more of a learn-it-all culture than a know-it-all culture.”

The article by Aine Cain on Business Insider A Facebook exec explains why she doesn’t hire ‘the smartest person in the room’ — and the questions she asks to weed them out is why the most important trait VP of HR Janelle Gale looks for in job candidates is curiosity:

“We look for learners, people who are acquainted to learning fast, are intellectually curious, and constantly looking to expand their knowledge,” she told Business Insider. “They’re actively seeking feedback and they’re open to it.

“We need people who are looking to incorporate new behaviors, new information, and new data, into their repertoire and skills.”

“The ability to incorporate new knowledge and information into what you’re doing allows us to move faster, because you’re learning faster.”

Curiosity is a strong desire to know or learn something. If someone drops the old proverb Curiosity killed the cat you can counter with But satisfaction brought him back.

While free food and drink and foosball tables are the obvious trappings of a successful tech company like Google if you look deeper you will find lecture series, access to proprietary databases, online courses, tuition reimbursement and a whole host of ways to nurture curiosity in a company designed to learn.

So when you are talking to people from hot new startups or visiting them ask the question, “What are you doing to help stimulate the curiosity of your staff?” Be curious about how others nurture curiosity, you’ll undoubtedly learn something you can apply to your own company. And be sure to share what you’re doing in your company.




Better lucky than good?


Guy Raz, who hosts the podcast How I Built This on National Public Radio, always asks the founders he interviews the same last question: How much did luck have to do with your success? I haven’t heard a founder yet say “nothing” but their answers do vary. Good timing is a common answer. I know I’ve been too early: iShop, a location-based app for retail shopping was too far ahead of its time in 2002 and Endorfyn, a mobile app to help people find the latest works by their favorite artists was too late – fans were to used using Twitter or Facebook to fulfill that need by the time we launched.

I’m a firm believer that founders tend to make their own luck and The Wall Street Journal article To Be Successful, Make Your Own Luck by Janice Kaplan and Barnaby Marsh comes to the same conclusion.

Luck occurs at the intersection of random chance, talent and hard work. There may not be much you can do about the first part of that equation, but there’s a lot you can do about the other two. People who have a talent for making luck for themselves grab the unexpected opportunities that come along.

The authors have three simple rules to help generate luck:

  1. Pay attention: The most important talent anyone who seems lucky possesses is the ability to pay attention on many levels and to notice opportunities. I’d add to this “get out of your comfort zone.” Traveling to offbeat places, reading books you’d never choose for yourself, attending meetings you normally wouldn’t go to. There’s a lot of way to get out of your rut and out of the office that increase the chances luck will run into you.
  2. Change the odds: Caltech physicist Leonard Mlodinow says one of the best ways to improve your luck is to keep taking chances. You have to keep trying and accepting failure, because the more at-bats you have, the more likely you are to get a hit, no matter what your skill. I would add to that swing for the fences. Founders need to think big to break through all the noise. I’ve yet to meet a successful founder who thought small!
  3. Think yourself lucky. Psychologist Martin Seligman says if he were looking for a lucky person, “the number one ingredient that I’d select for would be optimism.” I‘ve found many founders to be optimistic, some blindly so. But tackling a startup requires you to be optimistic, as the odds are against you. You really need to bump up against the edge of arrogance to convince the naysayers you are not crazy!

Out of the three factors that contribute to luck – random chance, talent, and hard work you have no control over the first two. But you certainly can control the last – hard work. I’ve found that successful founders work incredibly hard, far harder than their colleagues or competitors, just as the most successful athletes like Tom Brady, the GOAT (Greatest of All Time) and Michael Jordan, the GOAT of basketball. They outworked the competition despite having a lot of talent to start with.

If these ideas resonate with you read the new book How Luck Happens: Using the Science of Luck to Transform Work, Love and Life by the authors of the Journal article, Kaplan and Marsh. Personally I’m quite interested to read what else that have to say about the science of luck, which sounds like an oxymoron, but isn’t. At the least do keep the sub-title of their book in mind: Stories about getting lucky are common in the business world, but attributing success to random chance is misleading.