Uncertainty is an Innovator Superpower

Uncertainty is kryptonite for corporate managers, however, and that needs to be addressed.

In this, the buzzword apocalypse, we’re all innovating, being disrupted, and boldly marching into a future where everything will be new, different, and better. Except that we’re not. CEOs may be talking the talk, but most organizations aren’t ready to risk walking the walk. This, unfortunately, makes sense.

There are two key barriers: a lack of training and an aversion to risk. Career success in a big organization is usually tied to performing clearly defined tasks well. Successful innovation is often random and messy.

The future is hard to predict and there are a lot of things that can go wrong. Too many folks think working with innovation is either a matter of trying hard enough – or something to be avoided. It is hard to blame them.

The “trying to plan your way out of uncertainty” trap

A big corporate recently announced the launch of a startup accelerator with a difference. Their innovation: they will choose the participating companies carefully. They will devote all of 2018 to selecting the right handful of startups so they can avoid picking the wrong ones.

Any intern at an accelerator could tell the corporate in question that they’re wasting their time, but the trap they’ve fallen into is difficult for many corporates to avoid. The media make it sound like there are great startups everywhere, but startups are really hard to build. My guess is that there are more startup accelerators than great startups.

The gap between the C-Suite and middle management

The brave speeches CEOs give about innovation often mention the need to push decision-making further down into the organization. But their employees aren’t stupid. They know how big companies work. They know that innovation is a risky business with plenty of opportunities to guess wrong. They also know that mistakes get punished.

Did you really say Steve Jobs?

Poor Steve Jobs gets named over and over in these speeches, but no one ever talks about the Newton. (The what? Exactly. Go Google it.) They seldom mention that his own board of directors fired him. They assume that no one in the audience has read how he could be a nightmare as a boss.

Acknowledge the lack of incentives for the people taking the risks

Middle managers aren’t stupid. They know the odds of hitting a homerun like the iPod are absurdly long. They know innovation often requires working in a minefield of conflicting stakeholder interests. They know success takes time – and that any success produced by the risks they take likely will come on their successor’s watch.

Acknowledge their fear that innovation is dangerous for their career prospects. Give them room to make mistakes. Praise them publicly for taking risks.

Train them

Teach your middle managers to make decisions on the basis of imperfect data. Few of the people who will have to do the innovating have any training in innovation beyond the occasional magazine article. Send them to hands-on workshops. Have them work with actual startups.

Network them

Expand their personal networks to include people who effectively manage uncertainty. Most of the people they know work at the same company. Startups and innovators are used to uncertainty, to not having all the answers. Have your middle managers work with them as mentors, startup competition judges, and at corporate-startup matchmaking events to familiarize them with uncertainty – at a safe arm’s distance.

Let them self-select

Let your innovators volunteer. According to the Kauffmann Foundation, the most successful entrepreneurs are over 40. Every firm has a few risk takers hidden amongst the risk-averse majority. They often leave big corporations that can’t or won’t innovate to create the innovation they wanted to see.

If you train them, network them, and give them the opportunity, they may turn uncertainty into a superpower for you, instead watching them walk away to use their superpowers for themselves or someone else.

Mentor Match Is Overrated

Sometimes You Don’t Need To Be Understood

Storm 4

I find fashion startups hard to work with because there are so many ways to fail. Do everything right and somehow something bad always seems to trip you up. They also attract hard-to-work-with personalities. Burned fingers make me wary.

This goes part way to explaining why one of my favorite startups spent the first four weeks of an accelerator learning to tell me – and eventually themselves – that they weren’t a fashion startup. They’re an e-commerce logistics startup, a sector I like.

Four years later they’re doing quite well. Their customers are happy. Their investors are happy. They’re happy, and so am I. They’re not a fashion startup.

Avoid startup huggers, unless a hug is what you need

Your time is painfully short and you need to cover ground as quickly as possible. A lot of mentors are in the game because it’s exciting and fun and that’s fine – as long as they add value. Their support needs to help you move forward.

Some days are harder than others and a pat on the back or thumbs up can really help. Accept a hug when you need a hug, but don’t be needy. If they want to hear your pitch just to hear your pitch, consider moving on. Get stuff done. It’ll make you feel better.

Resistance can be good

Sometimes what you need is a grumpy, old mentor who doesn’t get you or your idea. Maybe you’re like the sensor company I worked with recently, that couldn’t understand the pushback to their contactless payment technology.

I told them what others wouldn’t. The common perception is that the breakthrough for their technology has been ‘right around the corner’ for twenty years. We don’t care that it’s big in Japan. Now they start their conversations by addressing the elephant on the table. It seems to be working for them.

Not everyone will get you – and that’s good

I’ve pitched a concept for the last year that people either get or don’t get. Buy-in seems to be immediate and intuitive – or not at all. Convincing people who don’t get it right away is hard, but I’m closer than I was three months ago. My message is sharper now.

Sometimes you need to be forced to explain yourself until the person across the table understands. People who’ve drunk the Kool-Aid aren’t always the ones who can help most. Sometimes you need to be misunderstood, if only because resistance can make you stronger.

Mentor Archetypes – Service Providers

Founders seem to draw so much attention that it often blinds us to the crowd of others whose efforts are essential to turning the founder’s vision into reality. One group that definitely doesn’t get enough love is the service providers. They get accused of charging too much, loitering at events looking for new clients, and they wear suits. Ouch.

Common perception, meet reality

The suits do make them stick out. I’ve seen lawyers wear sweaters, but accountants aren’t going to show up at an event on a skateboard. You probably don’t want them to. The suit is their uniform, the same way the developers’ t-shirt and flip-flops are. Look past the clothes, especially the tie.

Are they on the lookout for new business? Sure. Everyone’s looking for something. You want a smart money investor. The next guy wants a rock star developer. The woman next to you wants to hire a SAAS sales expert. How they go about finding new business and how you react to them matters.

The good ones are problem solvers – and you have plenty

Odds are that you need more of their advice than you realize. An absurd number of startups either don’t have founders’ agreements or signed papers that cause trouble when a founder wants to leave, you want to raise money, or your freedom to operate is being challenged. Everything’s good right now? Give it a day or two. Things move quickly with startups.

What can you get for free?

The answer is a lot. Think of service providers as the original content marketers. Another option is to think of them as thesis advisors: they can help you define your questions and point you in the direction of where to find the answers.

So you’re not in the market for their services

The good ones know a lot of people and can make introductions, even if you’re not in the market for legal advice. Many of them know a lot more about your business than you would think. You can pretty up slides, but you can’t hide the real numbers from your accountant. The accountants know who is making money and who is about to run out. The lawyers know who signed a rotten term sheet and who was smart. The IPR specialist knows who is about to lose their shirt in China.

The right service provider can be a great mentor

We’ll return to this subject later, because there’s a lot that smart startups can gain from getting close to the right service providers. They catch a lot of heat from people in the startup community, but the ‘suits’ can help create a lot of value. Ignore them and you may be missing out.

Mentor Archetypes – Entrepreneurs: The Very Bad and The Ugly

GothenburgIceLet me introduce the first mentor archetype with a cautionary tale. Entrepreneurs, especially serial entrepreneurs, are the mentor rock stars and I know many that are awesome startup mentors. They’ve been there. They’ve done it. They’ve proved they know how to succeed. Sometimes they’re right for your company – and sometimes they’re not.

‘The Good’

The good ones have startup experience relevant to your situation. They like giving back to the community. Lots of them are angel investors. They usually have great networks that they can share. Many are looking for their next project. If you find the right one, it could be a match made in heaven.

‘The Bad’

While good entrepreneur mentors are awesome, but I’ve seen bad ones be disastrous. Their badness comes in many varieties. There are know-it-alls, yesterday’s men, Shark Tank wannabes, limelight seekers, and many more.


Mentors do a lot of talking, but we do try to listen and we try stick to what we know. The entrepreneur mentor know-it-all is quick to cut you off. They say ‘me’, ‘my’, and ‘I’ more than most people. They want to talk about ‘my exit’, ‘my vision’, ‘my cool spouse, kids, car, gadgets’, ‘my amazing offer’, and they know exactly what you should do.

‘Yesterday’s Man’

Yesterday’s Man has credibility, because he’s ‘been there’, even if ‘there’ was ten, fifteen, or twenty years ago under completely different market conditions with completely different business models.

Getting lucky once doesn’t make you Steve Jobs. A lot of things have to go right for a startup to be a big success. Jobs was smart, but he worked with smart people in an industry that perfectly matched his talents at a time when explosive growth was possible.

Yesterday’s Man often wants you build your startup the way he built his, but business models have changed since a lot of these people hit it big. Ask yourself whether it makes sense. What did your phone look like ten years ago? You may be able to go further on a six-figure seed round, than Yesterday’s Man did with millions.

‘Shark Tank Wannabes’

I love Shark Tank, but I recognize that it is entertainment. Some mentors think their prior success marks them out as master negotiators. The art of the deal can be complex. If it was simple, there would not be so many books on the subject.

Many Shark Tank wannabes give bad advice on the ‘be a tough negotiator’ theme. They encourage you to make absurd demands and take the hard line. Sometimes standing your ground is the right thing to do, but it’s an easy course to advocate when you don’t have any skin in the game.

‘Limelight Seekers’

Success is intoxicating and a lot of successful entrepreneurs want back in the game once they leave the successful company they started. Some of them are doing it because they like being respected. They like being called rock stars. They like being adored. You don’t want to be their soapbox. Find someone that really wants to help you.

Channeling Tolstoy

All good mentors are alike; each bad mentor is bad in his own way. There are lots of ways to be led astray that I’ll leave for later. ‘Amazing’ offers, exploding offers, empty promises, long sidetracks, and their many cousins are all time wasters. If you’re unlucky, they are worse.

Look both ways before you cross the road

Rock star serial entrepreneurs can be perfect for your startup. They are great for introductions to mentors, business developers, software developers, corporates, investors, advisors, advisory boards, and more. Sometimes they really do have the answers to your problems. And sometimes they don’t.

Eight Mentor Archetypes You Need to Know

Who are we?
Mentors help startups meet all sorts of challenges, but finding the right ones to help your startup can be hard. It is a lot easier to know how and whether we can help you, if you know who we are, what we can do, and why we do it.

Know how to profile your mentors
Identifying which we profile fit is powerful and can be very straightforward:

“Anne, an ex-McKinsey consultant and former startup CFO, recently was part of a profitable exit and is now an angel investor. She wants three things:
• to meet startups that match her investment profile,
• to network with experienced angels to learn and perhaps co-invest, and
• to give back to the ecosystem.
Anne is demanding, detail-oriented, asks tough questions, and is good at getting startups to understand what they need to do to attract investors.”

How do you get a mentor to help you?
What should you do if you want Anne to help you? Do you have anything to offer her in return? How do you get from not knowing Anne exists or what she can do to a position where you can meet her and convince her to invest time and effort in helping you?

Start by using archetypes to analyze the mentor
Here are eight basic archetypes, with very brief descriptions, to help you categorize mentors. We often fit into more than one category, because we’re human, and therefore complicated.

Entrepreneur – Often the most coveted, but can include out-sized egos and opinionated people whose ‘lessons learned’ are out of date.
Investor – Usually looking for interesting investment opportunities. Used to being flattered.
Service Provider – Lawyers, accountants, bankers, and IP specialists. Good ones tell you how to make things possible instead of telling you they can’t be done.
Startup Enthusiast – We often fit more than one archetype. We are often in it for personal reasons as well as business. Some mentors just love the industry.
Board Professional – Includes consultants and can bring lots of experience and big networks.
Academic – Often have interesting analysis and access to relevant resources.
Corporate – Increasingly active partners. Many are still learning to work with startups. Can bring big scale to sales and much else besides.
Ecosystem Professional – The ecosystem is developing and specializing quickly. The people who run co-working spaces, incubators, accelerators, et.al., often have very relevant networks.

How to reward your mentor
Anne, the mentor profiled above, is looking for introductions to interesting startups and other investors. You probably know people you can introduce. Your startup may be a match for her investing profile or you may know one that is. You may be working with other investors she would like to meet.

Give to get
Any one of these three things may be the hook that gets you talking. Your ability to give her something she wants may help you get her to stick around to help you get what you need.

Match us to the task
Chemistry plays just as big a part as qualifications in mentoring, just like is does in dating. We will go into greater depth on the different archetypes later. Much depends on the challenge, the situation, the circumstances, and the match. Knowing whom you’re talking to early on can give you a significant edge on achieving the outcome you desire.

Who Are These Mentors?

Four questions to ask yourself about your mentors

Mentors do not come in one-size-fits-all packaging. Our backgrounds vary, our skills vary, and, quite naturally, our motivations vary. Understanding us, your mentors, requires looking past the standard answers and asking yourself:

  • Who are we?
  • What can we add?
  • What do we want?
  • What can you give us?

Archetypes are key to understanding mentors

The answers to these questions come easier if you categorize your mentors. The individual mentor often falls into more than one category. There is plenty of overlap, but the differences between us are often key. We include investors, service providers, corporates, consultants, and academics, to name just a few.

Match the mentor to the task

Of these, the serial entrepreneur is often the most coveted, but mentoring is very individual. Success depends on the challenge, the situation, the circumstances, and not least, the match. Sometimes the perfect mentor is who you initially least expect it be.

It’s not a task, it’s a tool

Taking the time to analyze your mentors often ranks low. The big list of ‘Must-Do-Tasks’ doesn’t leave a lot of room for ‘Nice-to-Do-Tasks’. This brings up one of the nice things about this job: it falls into the ‘Something-That-Makes-My-Life-Easier’ category. Figuring out who can help you with what saves you time so you can go faster.

Don’t do what mentors can do better, faster

To those who would say they’re too busy trying to grow great companies, the answer is simple. If you’re not giving mentors the attention we deserve, you’re not just missing out on something that could help you grow faster. You’re slowing yourself down by spending time on things that we could be doing for you. Mentoring is a very effective way to get what you want. We’re flexible. We scale.

What next?

How to do it, you ask? I’m going to examine that in greater depth. I’ve been doing this for a while, and I’ve seen it done a lot of ways. There’s data, my opinions, other people’s opinions, and all sorts of war stories. It’s going to be fun.