Startup Mentoring: a delicate balance of creative destruction
Tuesday Mar 6, 2012 by Fred Destin - Partner, Atlas Venture
I have been involved in many environments in which mentoring is a core part of the value proposition. Seedcamp or TechStars succeed almost exclusively on the quality of their mentoring. As a board member I try to be a good sounding board, a good partner and occasionally, when the situation warrants it, a good mentor. In any event, I have derived a clear conviction that good mentoring is a scarce resource that needs to be nurtured and developed in all of us. This is my (evolving) philosophy on mentoring startups; it's a personal one that fits my style and may not work for you, but I hope you enjoy it and find the time to share your mentoring tips too.
The damages of horrible mentoring
I am also writing this because I have seen some pretty atrocious mentoring over the years, and I want entrepreneurs to be able to recognize it. "This will never work!". "You need to monetize early or no one will fund your business !" It'd be funny if it did not end up confusing the hell out of founders and leaving a sour taste in their mouth. I don't want to embarrass anyone but it's ranged from "mobile apps absolutely need to be sold through the operator and your number one objective should be to get on their deck" (3 years ago, admittedly) to "I know this is a dev-focused product but you need a high level GUI so you can go demonstrate the value of this testing suite to the CFO and the CEO!" and other often dumb, always definitive advice delivered with aplomb of one who does not have to live with it.
Turns out, good mentoring is hard.
Step 1: Establish a trusted connection
Your mentee may be impressed by who you are and not want to disappoint you. He/She may not want to waste your time and move quickly to getting practical advice on tactical issues that they face. He/She may simply have no idea what to expect from mentoring and have the wrong agenda in mind. Step one in mentoring is establishing a protected, trusting environment in which your protege will feel free to quickly dig into the important issues, expose doubts and shortcomings and be disposed to make real progress. Your job as mentor is to make the person feel relaxed and intent on thinking through their own business issues instead of her burgeoning relationship with you. Do a quick intro, explain simply why you enjoy mentoring talent, talk plainly about some failures and some success stories that are contextually relevant. Make it clear this is about him/her, this is behind closed doors and all about making real progress.
Most projects start as poorly baked ideas that need a lot of work and refinement to achieve the appropriate form. This is generally true of all early projects. The faster you can get past the initial stage ("let me convince you that my idea is great") to the construction phase ("let me exchange with you to make this thing better"), the more benefit you will both derive from the interaction.
Step 2: Open your brain and understand the context
I always say mentoring requires intense frontal cortex activity. If you want to be helpful to someone, you're not going to achieve that just by rehashing experiences that worked for you. Step two is gaining an accelerated understanding of the unique person you are dealing with and the unique problems they are facing.
Ask the person in front of you what it is they do and what they are dealing with. For as long as you can hold it, don't project any of what you know or think you know. Calm the impulse you have to be immediately adding value.
Think very, very hard about the business concept you are being presented with and try to gain a 360 degree understanding of the problem at hand. You need to understand target customers or users, technology and product, team dynamics, go-to-market issues, value proposition and brand, and everything else that composes a new business concept.
Most importantly, you need to understand the person you are dealing, from what angle they view the world, how self aware they are, how far they have come in understanding their own strengths and limitations in relation to the project they are building. You need to discern what part of the discourse they have internalized and what part is a rehash of advice they have read or received but that they do not quite know how to handle (yet). Take in deeply the individual you are talking to, his/her style, and his/her language.
This is partly why good mentoring is an exhausting activity. You need ever neuron alert and ready to receive information, from objective facts to subtle physical cues about your mentee. Take it all in, take a step back, process.
Step 3: Frame & reframe
I find that time and again when I work with someone, the key to success lies in understanding what problem you are trying to solve. It's fairly systematic that a young startup will want straight answers to topics such as "how do we launch successfully" or "what do you think go our pricing model". Most of the time it's useful to take a step back and ask: "what question are you really trying to answer here?" If you get a question about pricing, the right place to start is probably "take me through your customer value proposition step by step." If you get a question about launch, the right question is probably "who are you targeting and why?" You get the picture. It's your job often to help the entrepreneur take a step back and think through the process by which they ultimately come to the right question / answer.
Step 4: Dig and deconstruct
Whilst a bit of open ended thinking might be useful, I find that generally it is much better to dig hard and continuously on a specific strand to force yourself and the entrepreneur to rigorously think through an issue. If we continue with the pricing discussion as an example, you will want to go three levels deep: How did you come up with the suggested pricing? Are there analogs that are useful given your target customers? Are people used to buying this way? Do you know how much your target group spends every year on technology solutions? How they budget? Where the bulk of their spend goes? And so on and so forth. It's very rarely about giving answers, it's usually about identifying shortcomings in the current approach or suggesting useful frameworks to define and test assumptions. You probably know half the time what the right answer is going to be : it does not matter. It is not about YOU.
I will often have in the back of my head some frameworks that I find highly reusable, such as Dave McClure's startup metrics for pirates or David Skok's SaaS Series, SG Blank's work or the Business Model Canvas. But I never use them overtly. I try to use common sense and discovery with the person I am mentoring to help frame the debate. I might direct them after the fact to the relevant material so they can internalize the concepts and re-use them. But every person / team / market is different and frameworks are often misused as recipes. They end up killing creative thinking (the "Curse of the Consultant").
Step 5: Express yourself
Ultimately our gut and experience help us cut through issues faster. Whilst for most of my mentoring work I will try not to project myself into a situation, I am not there to grinfuck people either. At some point, I will tell the mentee that I am putting back the "Fred Destin Hat" back on and express clearly my opinion. Here are three examples from recent TechStars sessions:
* I think your product design is poor and I am concerned that you do not have enough product sense within the team as it currently stands to solve that.
* I am concerned that you are doing way too much and will fail and if I were you I would focus all my efforts in the next 6 months on X.
* I find your pricing offensive and think you are taking too much margin from your customers.
Ultimately you're not doing anyone a service by being a cheerleader and not telling entrepreneurs when you think they are erring. The important thing is to clearly identify these types of statement as your opinions rather than facts. Your competence and experience make you fallible in different ways. But let's not confuse being founder friendly with always being friendly with founders :-)
How to be a Good Mentor
* Treat every situation as new
* Forget what you think you know
* Make a real effort to understand the tech, product and market of your mentee
* Help the entrepreneur ask themselves the right questions
* Don't hesitate to reframe
* Focus on providing a framework of discovery rather than answers
* Challenge hard and systematically what you think are failures in the thinking process
* Talk plain English, use simple concepts
* Limit the scope of your advice to actionable items
* Make it real and directly applicable to the problem at hand
* Be intellectually rigorous
* Be respectful but tough
* Repeat the mantra: "this is not about you"
How to be a Crap Mentor
* Don't listen
* Be normative in your advice
* Rely too much on your own experience
* Apply recipes
* Show how smart you are
* Keep asking the entrepreneur to explain their business model to you
* Ask for equity in the first session (Scumbag Mentors on the loose)
Mentoring according to TechStars
Dave Cohen has written a great list which he dubbed the mentor manifesto (I use small letters so it does not get confused with the real original Mentor Manifesto, rspct). Republishing here for your reading pleasure:
* Be Socratic
* Expect nothing in return (you’ll be delighted with what you do get back).
* Be authentic / practice what you preach.
* Be direct.
* Tell the truth, however hard.
* Listen too. The best mentor relationships eventually become two-way.
* Be responsive.
* Adopt at least one company every single year. Experience counts.
* Clearly separate opinion from fact.
* Hold information in confidence.
* Clearly commit to mentor or do not. Either is fine.
* Know what you don’t know. Say I don’t know when you don’t know. “I don’t know” is preferable to bravado.
* Guide, don’t control. Teams must make their own decisions.
* Guide but never tell them what to do. Understand that it’s their company, not yours.
* Accept and communicate with other mentors that get involved.
* Be optimistic.
* Provide specific actionable advice, don’t be vague.
* Be challenging/robust but never destructive.
* Have empathy. Remember that startups are hard.
Fred Destin is a Partner with Atlas Venture in Cambridge, MA. You can find this blog post, as well as additional content on his blog located here. You can also follow Fred on Twitter (@fdestin) by clicking here.
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