A few tips on mentor meetings



Most founders handle mentor meetings just fine, as they’ve had experience with business plan competitions, meetings with investors, etc. But here a few tips to keep in mind:

  1. Research the background of your mentors, so you know what areas they can help you with.
  2.  When introducing yourself, focus on the experience and expertise most relevant to your venture. The only exception to this might be things that you have in common with your mentors, such as where you went to school. Commonalities help build relationships.
  3. When asked a question, answer it directly and immediately, don’t go off on a tangent or say “before I answer that let me explain X…” Use active listening: repeat back the question, asking if you understood the question.
  4. Don’t interrupt others when they are speaking! You only learn when you are listening, not when you are talking.
  5. Don’t dominate the conversation – make sure your co-founder(s) and the mentors get plenty of air time.
  6. Use the whiteboard or flip chart, it helps focus everyone’s attention. You can take a photo of it at the end of the session to aid in your note taking. It’s ok to ask others to step up to use it to illustrate what they are saying – don’t try to own it.
  7. Don’t rely on PowerPoint or other presentation software. Mentoring is about conversations and interactions. The exception to this is when you are specifically asking for feedback on an investor pitch.
  8. Follow up the meeting with agreed upon next steps and a thank you to mentors

Why assigning homework works



It’s a truism that you should judge people more on their actions than their words, but it continually surprises me that founders interviewing employees, bus dev execs working with prospective partners, and others in the startup ecosystem tend to focus far more on talk than action.

Just in the past week I’ve read two articles mentioning how hard it is to judge job candidates based on a half-hour interview. This appalls me! No one should hire anyone based on a half hour interview! First of all, best practice is a series of interviews: hiring manager, potential colleagues, HR (assuming you have such a person), and those known in the company for their interviewing and personnel judgement skills.

But interviewing tends to be just questions and answers. What I have found works far better are two types of exercises: stand and deliver and homework exercises.

Stand and deliver and the case method

For me sales people are the hardest to evaluate. After all, if they can’t sell themselves, how could they ever succeed in selling anything else? But one way to judge them is to actually ask them to pitch you on a product, exactly as if you were a prospective customer. And like a prospective customer you should interrupt them with objections, to see how they both handle being interrupted and how they address the objections. You can ask them to pitch you on any product or service they have sold in the past. If they can’t convince you to buy their pitch, why should you hire them? An even better test is to ask them to pitch you on your product. That way you’ll see if they have done their homework on your company, product and competition.

The stand and deliver technique is not limited to sales candidates. I’ve used it for product managers, marketers, and others. For example, with a product manager I’ll give them an actual case from the company, where, for example, we have to meet a deadline to demo a product at a trade show, but we are running behind schedule. What should they do? Cut features? Limit testing? Forget about optimizing performance? There is no right answer. But the goal is to put them into the shoes they are expected to fill and see how they walk in them. Again, you should pepper them with questions, just as they would be if in fact they were the product manager explaining to an engineer that his favorite feature had to be cut in order to meet a deadline.

By having a series of experiential interviews with various different people across the company one can gather valuable perspective on the job candidate. And that helps the candidate as well to understand the job they will be expected to perform.

Stand and deliver is a technique that isn’t limited to interviewing job candidates. It works equally well with mentees and prospective partners. I base my approach loosely on the Harvard Business School case method. I developed one of the first interactive business school cases with HBS and in the process learned enough to be dangerous about the case method. By while HBS uses it to educate I have used it to test the abilities of people to think on their feet and react to a real world problem, not a hypothetical situation nor something from their past experience.

Pioneered by HBS faculty and one of the highlights of the HBS experience, the case method is a profound educational innovation that presents the greatest challenges confronting leading companies, nonprofits, and government organizations—complete with the constraints and incomplete information found in real business issues—and places the student in the role of the decision maker. There are no simple solutions; yet through the dynamic process of exchanging perspectives, countering and defending points, and building on each other’s ideas, students become adept at analyzing issues, exercising judgment, and making difficult decisions—the hallmarks of skillful leadership.

The best results I’ve seen is where the mentee has stepped up to the whiteboard and diagramed his approach to solving the problem. Again, while words are important, actions and visuals are equally important. Make a whiteboard and markers available and see how many prospects make use of them when addressing the business case you drop them into.

Assigning homework

I’ve found that asking people – job candidates and prospective partners, even investors – to do some homework after a meeting to be a good test of at least two things: one, their level of interest, and two, their ability to understand what’s needed from them in the relationship, be it as employee, channel partner or investor.

Obviously people are busy and you can’t assign the equivalent of writing the great American novel, so make sure you assignment won’t take more than and hour or so and set a short deadline for it. Another thing you’ll learn – can this person make a deadline?!

I stole this idea from Forrester Research. I still remember how Josh Bernoff, one of the few people who have survived working for me in two different companies, told me how he had to prepare a presentation as part of his interview process at Forrester. Needless to say he got the job and became one of the most successful analysts at Forrester.

It can also be quite illuminating to see how people react to being given a homework assignment. For example, ask a prospective investor for the names of three CEOs of companies in their portfolio whom you can call to talk about their experience with their firm. What you’re looking for is, of course, an enthusiastic response, such as, “Glad to, we’re 100% referenceable,” as Bill Kaiser of Greylock once said to me.

As they say “talk is cheap” – so go beyond just talking to prospective candidates, partners, and investors, to stand and deliver, the case method, and assigning homework.

Best yet is actually doing something with people you intend to work with besides going out to dinner! For example, I’ve learned a great deal about people by traveling with them – how they handle the frustrations and boredom of travel, how they treat service personnel, and much more.

While traveling isn’t very practical, attending a local trade show, seminar or even a ballgame to see how your prospect behaves outside the office can often be a valuable supplement to an in-office talk session.

Mastering the Informational Interview



I often advise my mentees in very early stage companies, and I see a lot of stage zero companies at the MIT Venture Mentoring Service, to do informational interviews to gather first hand market research about their idea and to test its validity. Informational interviews are also a great way to network, as you shouldn’t conclude an interview without asking for other people you could talk with.

I’ve found that most successful people are glad to talk with budding entrepreneurs – so long as they don’t feel like they are being sold to – because they like to give back.

This article from Forbes Mastering the Informational Interview by David Schwab is a very good primer on how to conduct an informational interview. While it’s geared toward young professionals and students with one goal: to help make you a more viable candidate it’s a worthwhile read for budding entrepreneurs who aren’t looking for a job, but can benefit greatly from conducting an informational interview.

See also my post How to get meetings with people too busy to see you: do your homework!

He outlines four major tasks:

  1. Know How to Differentiate Yourself
  2. Social Media is the Best Interview Tool Ever, if you Use it Wisely
  3. Respect My Time, but Make It Work for You
  4. Always Look for Learning Opportunities

And of course, Mr. Schwab highlights the value of mentoring:

Mentorship is an excellent way to grow, learn and connect with others across your industry, but it takes effort from both parties. The younger professional needs to come to the table with questions, observations and ideas a mentor can respond to. Remember, it is not who you know, but who knows you.


Sample questions to ask:

  • Who are your mentors?

As the saying goes, Inside this room all we have is opinions; outside this room are the facts. So if you have a startup idea, get out of your office or apartment and start talking with people who can provide you valuable information that you can use to turn an idea into a viable product or service.



Tips for meetings with VIPS

I’ve had dozens and dozens of meetings with VCs and potential partners, including IBM, Apple, Microsoft, Fujitsu and many no longer with us like Lotus, WordPerfect and Ashton-Tate.

Here’s a few tips when meeting with these VIPs in their offices.

  • Get there early to observe the company culture. You can learn a lot by sitting and watching how people interact and what their demeanor is. Be sure to leave plenty of time to find visitor parking if you drive and allow time to find the office itself.
  • If you will be doing a presentation set up your laptop and make sure it works well with the video projector, including color and aspect ration. Test out any sounds in your presentation as well.
  • Bring dongles for connecting your laptop to the video projector. More time is wasted getting laptops to work with video projectors than any other aspect of meetings. Often larger companies will have someone knowledgeable around to help you,  but don’t count on it.
  • Bring printouts of your presentation just in case technology fails you. But DO NOT hand these out ahead of time or your audience will be skimming your presentation instead of listening to you.
  • It really helps to get to know the AA to the VIP you will be meeting with ahead of time. Admins keep schedules, arrange for conference rooms, troubleshoot video projectors and lots more. They can help make or break your meeting. Treat admin staff with the respect they deserve.
  • Leave just before your time is up – always leave them wanting more. If they want you to stay past the meeting close they will say so.
  • Make sure you have a call to action to close the meeting – even if it’s only to get the next meeting.
  • Follow up your meeting ASAP with an email summary. If something really good happens at the meeting, like a signed contract, follow up with a handwritten card.
  • See my previous post on why it’s beneficial to have two people from your company at VIP type meetings.

Tips for taking mealtime meetings

Everyone needs to eat, and everyone is very pressed for time. As a result, most business people tend to try to combine meals with meetings. I’m not fond of this practice, as I don’t believe people can really multi-task, so trying to eat, drink and carry on business at the same time tends to result in sub-optimal results in at least one domain. Going for coffee is a lot simpler than a meal. But if you have to have a mealtime meeting here’s some tips to help make it more effective.
Location – be careful not to choose a place frequented by competitors, investors or others you don’t want hearing your conversation; make sure it’s not hard to get to, and there’s parking and/or public transportation, so whomever you are meeting doesn’t waste time trying to find the place or find parking when they arrive. And end up being late.
Atmosphere – Quiet, but not too quiet – just enough music and other’s people’s talking to cover your conversation.
Pre-eating – Since it’s very hard to multi-task, I recommend that whatever the meal, you considering eating it beforehand, then order very lightly or just get a drink. That way you don’t end up talking with your mouth full, spilling your drink, getting ketchup on your tie and all the other clumsy stuff I’ve done while trying to eat a restaurant meal while holding a conversation or trying to demo a product on a crowded restaurant table.
If that’s too much for you, at least get the restaurant’s menu in advance (and send it to your meeting mates) so that time spent ordering can potentially be saved.
Get a reservation and while you are at it, ask for a booth in a quiet area.
If you requested the meeting pick up the check! But consider the advice given in this blog post about always buying the small meal.

How to get meetings with people too busy to see you: do your homework!


Steve Blank is one of the top educators of entrepreneurs in the U.S. if you don’t know his works you should. Start with his web site, move on to his books.

This article on Medium by Steve addresses one of the most common challenges founders and their directors of bus dev face: getting meetings with people too busy to see them. (And if you aren’t familiar with Medium, it’s a wellspring of great articles by founders and technologists like Steve Blank.)

I’ve tried to teach my mentees that when it comes to getting meetings you should think about what’s in it for the person you ware meeting with, not just what’s in it for you. In fact, I consider that a cornerstone not just of bus dev, but of business in general. But Steve refines this principle into one that’s more operational and more focused:

Steve filters the hundreds of meeting requests he gets from former students, entrepreneurs, and others with this rule:

who is offering to teach me something I don’t know.

This offer of teaching me something changes the agenda of the meeting from a one-way, you’re learning from me, to a two-way, we’re learning from each other.

It has another interesting consequence for those who are asking for the meeting — it forces them to think about what is it they know and what is it they have learned — and whether they can explain it to others in a way that’s both coherent and compelling.

The meeting requests that now jump to the top of my list are the few, very smart entrepreneurs who say, “I’d like to have coffee to bounce an idea off of you and in exchange I’ll tell you all about what we learned about xx.

Of course, offering to teach someone something they don’t know requires you to do your homework: what is that they know? What is it they would be interested in learning about? Studytheir LinkedIn profile, their bio on their web site or on Wikipedia, talk to other people who know them, read their blog or posts on Twitter or Medium: do your homework! Bill Belichick,  Coach of the New England Patriots preaches to his team: “Do Your Job!”
I preach to entrepreneurs getting ready for meetings or presentations of any kind:
Do Your HomeWork! You can think of this as Bayle’s corollary to Blank’s law of getting a meeting with people to busy to seeyou.

“Drawing conclusions on the wall”

No, this is not a post about Bob Dylan lyrics, much as I love and admire Dylan’s lyrics and music, and this line is from one of my favorite songs. It’s about what I consider unusual behavior on the part of entrepreneurs and mentors.

Virtually all MIT VMS meetings are held in conference rooms painted with whiteboard paint and supplied with markers. Yet over years of meetings virtually no entrepreneurs and very few mentors every step up to whiteboard to illustrate their thoughts. And yet you can’t go into any tech company without either seeing more whiteboards than the average sports bar has TV screens or whiteboard painted walls – all filled with diagrams, equations, to do lists, etc.

It hadn’t occurred to me until now talk to anyone at VMS about this – perhaps they need to write ‘Please feel free to draw, scribble or write on this wall!” in large letters on the walls as perhaps the entrepreneurs don’t realize they can.

Virtually all my mentees come armed with pitch decks, which they want the mentors to review. And often times these decks are well done and spark valuable discussion, though often that discussion tends to derail the slide presentation and we don’t get to the end of it even in a 90 minute session.

But I was really was impressed the other day when I mentored the head of a team working on a complex agricultural technology product. He came to the meeting without any deck or handout, but was very articulate. When I asked a specific question about data flow and capture, he simply took out a pen and drew me a diagram which he explained as he drew. Believe me, he shouldn’t give up his day job as an MIT scientist to become a graphic artist, but his simple sketch was worth at least 1,500 words if not the canonical 1,000 credited to a picture.

Why is that? Because startups and product development are by their nature dynamic processes, the operational definition being that discrete actions take place over time, and time is a very significant variable. Why then show it in a static slide? Step up to the whiteboard or pull out your notebook and diagram the process. Or if you’re skilled with presentation software use its animation tools to demonstrate the flow of your product or how your business will develop over time or how different elements of the product or service interact.

IMHO the plethora of business plan competitions and pitch contests have gotten entrepreneurs into a “canned” presentation mode. Many of these events don’t have any time for Q & A, as they have as many as eight or more companies pitching back to back. As a result the skill of thinking on your feet, and better yet, explaining and persuading on your feet, is not getting developed as it should.

So yes, I realize you need your pitch decks for contests and for investors, but when it comes to a mentoring session try leaving that deck on your computer and discuss your business, stepping up to the whiteboard or drawing in your notebook to illustrate your points. Or for those of you skilled with drawing tools on your laptop or tablet, use those.

The key point is that mentoring is about interaction, it’s a dialog, not a monolog. It’s not a pitch contest. We are not there to judge you, but to give you advice, feedback, and the benefit of our experience. And most of all, to help you to succeed. One step in becoming successful is learning how to communicate visually and in real time, because that’s what you’ll be doing once you are actually running your company rather than just pitching it.


Why two people at a meeting are better than one

Early on in startups partners tend to do almost everything together. As the company grows they have to learn to delegate and specialize, otherwise they are not optimizing their time.

But there is at least one circumstance where it’s highly beneficial to have more than one member of the startup team: key meetings, such as those with potential investors, partners or customers.

There are several benefits to having two of your team at the meeting:

  1. While one team member talks the other can observe the audience and see what resonates with them and where they may lost interest or get confused. I’d advise developing a signaling system to that the observer can warn the other team member if he’s losing the audience. It helps to sit next to each other, even if all you do is kick them under the table, rather than pass them a note or type something on your laptop only they can see.
  2. I find the bigger the company – and I’ve dealt with very large ones, including IBM, Apple, Microsoft, Fujitsu, Ernst and You, Reed Elsevier, and many more – the more people they bring to the meeting. Though the younger the company the less the tendency to bring an army of employees to meet with a startup. So it can really help to have another team member, preferably one with complementary skills, so you can address the business questions while your partner addressed the tech questions or vice versa.
  3. As noted in the previous post on taking notes, one team member can take notes, while the other speaks or listens or you can trade of the note taking between you.
  4. If you are giving a demo or showing off a prototype one of you can be setting up the necessary equipment while the other keeps the meeting going. And again, once the presentation starts, the non-presenter should be observing the reaction of the audience.
  5. Finally when the meeting breaks up if there are two of you there’s a better chance of making a personal connection in the chit chat that inevitably follows a meeting.

Many people complain about meetings. And I agree there can be two many internal meetings, which can waste time and be unproductive. But you can’t have too many investors, customer or partner meetings (assuming you qualify the attendees ahead of time). You won’t always need a tag team to handle these important meetings, but it will help as you start the company and are still honing your story and your pitch.


Taking notes & underlining books

I’m a big believer in taking notes. Interestingly, so is my health care provider, Harvard Vanguard Medical Associates. For years my PCP (Principal Care Provider) typed away on his keyboard while talking with me. I was always impressed by his ability to pull up his notes from the last visit for his reference. And,of course, those notes were available to any other doctor in the HVMA system.

Lately HVMA has gotten even more sophisticated and addressed the one problem with having the PCP take notes: how can you pay full attention to the patient, especially their body language and demeanor, if you are typing away on your keyboard? Well now my PCP brings in a person with a laptop called a “scribe” and asks my permission for the scribe to take notes, which I always give. Occasionally he directs the scribe to record some specific findings. This enables him to pay full attention to me, while still having the advantage of having a complete record of the appointment.

So what does all this have to do with entrepreneurs? I have to admit that I have a bias against entrepreneurs who come to a meeting with nothing to write with, no paper, no pen, no laptop, no tablet. Now I realize these entrepreneurs are all far younger than I am – but so is my PCP – and have better memories, but I think this is a big mistake.

Taking notes not only give you a record of the important points – and I hope I make at least a couple during a mentoring session! – but it’s my opinion, and I believe studies bear this out, that the act of note taking actually improves one’s ability to retain and understand information.

Let me emphasize, entrepreneurs are not PCPs, they don’t need a full record of every meeting they have. But if you are an entrepreneur, I strongly recommend you take notes of key points during mentoring sessions, even if you have to ask your mentor to pause a moment while your note taking has a chance to catch up.

MIT VMS has a great way of encouraging this behavior – they require that the entrepreneurs submit a written summary of the meeting to the office after the meeting. I see these summaries and some are practically transcripts and it’s clear that the entrepreneurs absorbed everything the mentoring team told them likes sponges, others are not as complete.

Keep in mind: you are not a stenographer. Your goal is just to capture phrases and key points for yourself and to share with colleagues. If there are two or more entrepreneurs at the meeting, one of you can take notes, or you can trade off this responsibility.

This doesn’t just go for mentor meetings – it goes for almost any business meeting: investors, partners, job candidates. Learn to take good notes, how to share them, how to organize them, and most of all how note taking can benefit your learning process.

Finally, for many of the same reasons I recommend when reading a business related or tech related book or document, you get out one or more highlighters. My former boss at MIT, Professor Jim Bruce, Director of Information Systems, was the grand master of highlighting. He had a set of about half a dozen different colored highlighters and every document that hit is desk was highlighted by a system I never learned. But I did learn that nothing every got by Jim and he was always on top of every element of running the IT systems for a large, complex institution like MIT.

If you pass your book or document along to others, those highlights of yours can also be helpful to your colleagues. Of course, modern word processors, like Microsoft Word, have a highlighting feature, so highlighting, like note taking doesn’t have to be confined to pen and paper.

So while you may have two or three degrees, your education is never over. As an entrepreneur you should always be learning, and note taking and high lighting are two techniques to help your learning process. If you didn’t learn these skills as a college student, start learning them now.





The virtual office

I was discussing with an entrepreneur today how much we like hotels as our virtual offices. Hotel lobbies often offer Wi-Fi, always have nice bathrooms, have comfortable furniture and relative peace and quiet. Great places to work, and good places to meet. Though be careful what you discuss, you have no idea who that person on the couch across from you is – they could be a competitor or an investor you may run into one day soon.

But don’t be a vampire. If you have friends or relatives who need a hotel, recommend the one where you occasionally hang out. Don’t abuse hotel’s generosity and try to repay it when you can. Patronize their restaurant, coffee shop, and even their gift shop, if you need the latest Wall Street Journal on paper.

The same goes for other places I’ve had lots of meetings at, including Starbucks and Panera. Frankly I’m not fond of the coffee at Starbucks or the food at Panera, but I always make sure to buy something when I’m borrowing their space.

Panera has risen to the top of my list given their free Wi-Fi and suburban parking lots. Though their locked up bathrooms requiring codes or passkeys are a hassle compared to hotels.

As an entrepreneur, particularly if you are flying solo, you need to stretch the dollar. Or as the old saying goes, squeeze the nickel so hard the buffalo grunts.

Obviously you can work out of your house, but if both you and your significant other are working at home then you may end up seeing more of each other than is comfortable. After all, isn’t it absence that makes the heart grow fonder?

And of course, if you are traveling, hotel lobbies and coffee shops can be a refreshing alternative to working in your hotel room.

And as a former librarian, I’d be remiss not to mention your local public library as a great place to work. Some even have conference rooms where you can meet. Virtually all of them have public access computers. But I have to admit, they do come up short in the food and refreshment department. My favorite library is the Cambridge Public LibraryCPL, built at a cost of something like $93 million and designed by one of my favorite architects, William Rawn Associates. It even has its own underground parking garage.

Where’s your favorite virtual office?