Startup Mentoring Sessions: How to get the most out of it.

Nov 29, 2012 · 11 min read · 7,773 views

Everyone is doing pitch training. Almost no-one does training for the mentoring session, but this is where most startups get the majority of their value. – Sitar Teli, Connect Ventures.

In the last 4 years I have been to countless mentoring sessions. I have been on both sides of the table and noticed a lot of mistakes done on both sides, often by myself. I wanted to share a few of my lessons i have made during those sessions. I hope it helps you getting more out of your mentoring sessions.

This blogpost is about mentoring session formats as you see in most incubators, startup weekends or acceleration events. Startups own a table, mentors circle in groups from startup to startup. This post is part of a two-blog series about this topic. This time I am focusing on the startup’s side of the table. Good Mentoring is about both sides of the table.

Dear Startups…

1. Work on your Attitude

I know you were just picked to join Seedcamp or Ycombinator or Techstars. You are right now in this extreme hype phase, this phase where things start to move, you want to meet all of Silicon Valley, right now. In the morning you were pitching in front of investors, now they put you down with worldly mentors… to talk… you don’t need words… you got words, loads of them… You want cash, need cash… want to get big… rush off… sky-rocket hockeystick! And you are an experienced entrepreneur anyway, you already build an successful agency, you are not like this other kids here, you have experience, more experience than whoever this guy is who is mentoring right now, you should have never applied to that b-level event……… And also you had really a long week preparing the talk next to all the normal crazy work, you traveled all night, you pitched all morning, you have office stress right now, you are tired……… Seriously cut that crap.

I have seen startups where some of the founders started fiddling on their phone, walked away to get themselves coffee, checked their emails, skype-chatted, looked bored into the corner, started side-talks. Honestly… don’t!… Pay attention or you just waste a big opportunity and look like an ignorant ass. Be present and use that opportunity to every extend possible.

2. Prepare! Know what you need

Prepare questions about each aspect of your company. Don’t try to come up with clever long-term questions about your international growth or optimizing your Series C. Focus on short-term problems you actually really face (or face in near future). Whenever you can focus on concerns that fundamentally question your startup.

Know whom – worldwide – you would love to have intros to. Who is the guru in your domain? Who would be the perfect advisors that could become angels ? Someone at that event might know that person.

Don’t come to just “get feedback”. Do your homework before or otherwise you are just going to waste everyone’s time.

Pro-Tip: Prepare a one-pager explaining your startup, your founders, what challenges you currently face and what kind of ressources or introductions you are looking for.

3. It’s YOUR table - take the lead

Own the table. Lead the conversation. It’s not the job of the mentors to judge you, roast you or take you apart. It’s their job to give you the knowhow you request. If you don’t take the initiative, a mentor will take it.

Dean and Vincent of Nuji - they never ever looked so not-hip again

Avoid repeating the same topics Especially when you are in an early stage with your startup many problems you have are big and friggin obvious. Every mentor will tend to ask about the same problems, press into the same open wound. Stop them. Admit the problem, thank for the feedback but ensure you discussed it with several mentors before and ask a specific different question. Get them to move on. Retake the lead.

If a mentor is disturbing your table - ask him politely to leave. It’s your time, your table, your rules.

4. How to start a session

Typical mentoring sessions are 15-30 minutes. That’s almost nothing - it will be quicker over than expected. Use the time and get as quickly as possible to the “value bits”.


Ask everybody on the table to introduce themselves and name their field of speciality. If someone joins late they should do that as soon as they sat down.

Explain the product in a nutshell. Don’t expect people to remember, there will be someone on the table happy about getting up to speed again. Also they are tired and for sure anyway confuse you with the social loyalty startup that has a similar name, and trust me there is one.

Agree together with the mentors what topic you want to focus on and what you want to get out of the session. Mentoring teams are usually mixed. Don’t worry if you want to focus just on (e.g.) PR because there is one great PR mentor on the table. It’s about you and your needs. The other mentors do understand it and are happy to learn from the PR person.

Pro-Tip: Have an ipad ready to show your product. Keep screenshots of the product on the iPad well… Most probably the WIFI won’t work at the venue. Additionally have the same screenshots on your iPhone for the discussions in the breaks.

Jakub Krzych of Adtaily wrote a very good and detailed summary about the optimal session process on the seedcamp blog, be sure to read it.

5. Shut up

You are not there to hear yourself talk. Keep your answers to the point, in most cases mentors don’t care about the details of your answer - if they do they will ask deeper anyway. They only want to know if you thought about it. Yes you do? Ok, let’s move on.

Important for strong co-founders: Don’t reiterate your co-founder’s answer just to add the missing 10% of the explaination. Don’t top-up your own knowhow to everything said. You are not there to learn from yourself – that’s just mental incest.

Shut up as often as you can. Every minute spent talking by you guys is a lost minute.

6. Learn to accept negative feedback

Startup-founders need to be stubborn and naive, otherwise they couldn’t start a startup in first place. But learn to take feedback and be ready to question your core-assumptions.

If you know a mentor is wrong - learn to let go. You are not there to convince mentors, you are there to learn from them. There might be millions of reasons why you and a mentor don’t agree with each other – but in any case it will eat up a lot of valuable time… Accept the other point of view, try to understand it, take notes, try to learn from it, move on.

It’s feedback, take it or leave it.

In many cases experienced people are right about their concerns – in some they are wrong.

In many cases you have a problem with your startup – in some cases the actual problem is how you currently communicate it.

7. Take notes

Too often I see founders going through 4-5 x 30 min mentoring sessions, with the assumption that they’ll just magically remember it. Some of the most valuable advice will be dropped in mere half-sentences, some of the best reasons for follow-ups will occur somewhere in the middle of a really really long day. Please have a piece of paper, and a pen at hand (no, your ipad isn’t sufficiently quick to record, and it’s disturbing).

Have the same person, writing stuff down, the same way for each session. Sort “applicable” vs “non-applicable” the next day.

(Thanks to @CsabaSol for pointing out this one)

8. Opinions – Loads of them

Very often people want to give you opinions… Always filter opinions from personal experiences and personal experiences from market facts.

“Well, opinions are like assholes, honey. Everybody’s got one and everybody thinks everybody else’s stinks.” – Henry Larson / Home for Holidays

Instead talking about opinions get them to talk about a real experiences they had. If they try to avoid it or talk about “normal people”, “real world” or “the average customer” file it as opinion and add it to the suggestion bin (as pictured below).

9. Applying advice

No mentor knows as much about your business as you do, but they still advice you. That’s neither good or bad, that’s just normal. Advice is not meant to be followed. Advice is meant to be understood and incorporated.

Never follow advice. Apply advice. – @nivi of

Sometimes given advice is just not suitable for the phase of your startup or it might just assume a bit too much of “a perfect world”.

Rob Fitzpatrick recommends in that very moment to simply ask “Would you recommend us to drop everything else right now and follow that advice?” - The usual answer goes along the lines of “… well not right now… but in a few months …after your series B round” Be careful how actionable the advice is meant to be.

10. Contradicting Feedback

During the time of your startup you will hear a lot of contradicting advice. Very clever, rich and experienced people will advice you to do completely opposite things.

The reason is simple: The judgement of EVERYBODY is limited to their subjective context.

The world-view, the values, the core beliefs of someone running an VC might be completely different from yours. Neither is wrong or right - it’s just differently biased. Try to decrypt the feedback given the background of the person.

Example: VCs always tend to focus on growth concerns like scaling customer acquisition for your “too-little-market” startup or want to dive into numbers about your made-up revenue model and push your product to be b2b as this would be better in the current market. Product people tend to freak out about the fact that your product is too visionary and not a real customer’s job.

Both will give you completely contradicting advice what to do next. And both are right from their point of view. Value their feedback, but understand in the context of their background.

11. Keep them working for you.

Exchange business cards after (or beginning of a session). Write down the reasons for followup. And do the follow up the very same (latest next day). Mention something they said or how they helped you. Ask very precisely for introductions or any other favour you might need at that moment.

Pro-Tip: I have seen several founders doing this very successfully: Create a newsletter of mentors and supporters willing to help you and keep them updated similar you would keep your advisory board updated. Ask pro-actively for support. I personally prefer newsletters (bcc-emails) over facebook groups as facebook groups live and die with critical mass and no-one wants to step into public posing with all the great contacts he has.

Update: Bonus - Learn from the best!

One of the best go-to people in London for advice and buttkicking - @geoffwatts, CEO of EDITD - allowed me to publish his presentation he does to new seedcamp recruits. It is a 15 minutes preparation for one of the toughest weeks in their startup career. He covers several parts here mentioned - but also several good extra details.

Download it here

More to come

As mentioned above this a two-post series. If you are interested to know how to be the perfect mentor i would recommend you to read the follow up post, coming very soon.

Please let me know if I forgot to mention any aspects via twitter. I would love to see this document becoming a living summary of best-practices. If you run an accelerator/incubator or events, let me know what I am missing that would help your startups. If you can send it to your teams, get them to feedback their experiences. I appreciate their input highly!

Until then, yours truly @andreasklinger