Startup Mentoring, the Socratic Way

 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. Below 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.

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 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 pitch phase (“let me convince you that my idea is great”) to the constructive 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 the individual you are talking to, her style, 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 fell 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 :-)

Mentoring is a process. None of us is the Oracle of Delphi, no matter how wise we think we are. And remember none is wiser than Socrates himself. Discuss.

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