How I streamline and “automate” giving one free mentoring session every day.

I’ve always believed in the power of mentoring, and although there is a limited amount of insight and expertise that can be transferred in a short period of time (my sessions are ~45 mins), I hope I can really add some value.

I’ve been mentoring with accelerators and directly with early-stage entrepreneurs for years, but while we were in particularly strict lockdown in the UK, I wanted to formalise it so that I made one hour a day available for free. I was spending 12 hours a day at my laptop, after all. Maybe I could use one of those hours to help others…?

But we all know how much pre- and post- call admin is actually involved in these things. I didn’t have the time for this “one hour” to bleed into two or three hours a day by the time all the organising, scheduling, and follow-up emails back and forth have been taken into account.

So, I automated pretty much everything except the actual conversation.

None of this is particularly high tech, but I hope it gives some insight into managing your time for those that have a lot of incoming requests.

This is where the, erm, “magic” happens…


  • I get lots of enquiries. I have a form on my site to filter out the occasional person I can’t help.
  • I send a link to book into my calendar.
  • I use Calendly to allow them to choose a slot, and it auto-creates a Zoom call.
  • I do the call, strictly finishing after 45 mins.
  • I send them a a follow up email 15 mins later.
  • All the “resources” section in my follow up email is from a regularly updated template text.

Total time a day = 1 hour. Processes and boundaries allow that not to creep to 2hrs a day.

Nearly 100 entrepreneurs have had value to date.


1 – THE ON-SITE FORM (0 mins once setup)

Firstly, the page in which I offer the free sessions has text which discourages the non-serious enquiries, or those I can’t really help (I’ll signpost them to more relevant resources if so). I only want to help people who are really interested in being better.

To achieve this a quick form (available as a plug-in on most website builders, or embeddable as a Google Form) then grabs some basic info about the entrepreneur and startup, and automatically emails it to me.

I have a quick look at any information that the entrepreneur has sent through, and decide if I can really offer value to them (which I think I can in 95% of cases).

2 – THE “HELLO” EMAIL (1 min)

I have a template email set up to send them a hello, let’s them know that I’ve checked out their idea/site, and that I’m looking forward to chatting to them. The email includes a link to book a slot in my calendar.

3 – CALENDLY (0 mins once setup)

Other booking software is available, but I’ve used Calendly for years. I pay $10-ish a month, and it’s worth every penny for the amount of time it saves me. It allows me to create a unique link for these mentoring calls to put in the email above. It also links with Zoom, and auto-creates the Google/iCal entries.

One really useful thing it does is that allows me to limit the hours in which my calendar is bookable (10am-6pm) for mentoring, but also only allows one session booking a day.

It books out an hour, but the text makes it clear that the actual session is only 45 mins. The remaining 15 mins is used for writing up notes, as you’ll see.

4 – THE CALL (45 mins)

Here’s the biggest time sink, but where all the value is for the entrepreneur. I have a rough structure and set of questions that I try to adhere to, to allow me to get the most insight into their business, and also give valuable feedback, all within 45 mins. But the reality is that I have to be flexible to each business. But there are usually common themes that often come up about validation and product-market-fit etc. After 40 mins I’m like a therapist, and gently point to the fact that we’re coming towards the end of our time, and ask if they have any final issues I can help them with.

5 – THE FOLLOW UP EMAIL (15 mins)

Immediately after the call, while it’s still fresh in my mind and on my notepad, I write an email that summarises what we discussed, and gives them a few questions, challenges, and offers to help in any specific ways if relevant. This is usually about 3 or 4 paragraphs, as that’s the limit of what can be covered in 45 mins.

However, below that I also copy in a lot of resources that regularly come up in such calls. I regularly help early stage product/tech businesses, so there’s some set text and video that is usually gets mentioned during the 45 mins. There’s also a bunch of links to blogposts and tweet threads that are particularly insightful about certain sectors and verticals. I have a few links about two-sided marketplaces, for example. These seem to be regular conversations (3 of the 5 sessions this week have been about two-sided marketplaces of varying kinds).

I maintain this Resources text as a Google Doc, and regularly refine and update it. It’s starting to get quite lengthy now, so I’m trying to slim it down a little, so as not to overwhelm people.

At the very bottom of this email I’ve put my Buy Me A Coffee link. I don’t expect anyone to do it, and I’ve no problem if they don’t, but about 30% do. So I’ve had a bunch of lockdown coffee off the back of it, at the very least!

I genuinely love helping, so this is its own reward, but the bonus caffeine helps…



In the last 12 weeks alone I’ve done an intro off the back of a call which has resulted in one getting his first commercial trial, and it’s with a £120m business, and also helped another one successfully pivot, and halt the decline of their business. I also received this Twitter DM…


I’ve also had a whole bunch of very grateful thank-you grateful emails.


I’m hoping to get better at automating the follow-up a month or two later to find out how useful my advice has been in real terms. I’m currently sending out a survey that they can fill in anonymously, but I need to automate it so that Zapier auto-sends a certain number of days after the mentoring call. I have all the mentees in a spreadsheet, so that should be fairly easy. Any other ideas here??

Although it’s not why I started doing it, I think there might be a small side-gig here. Quite a few people have asked me if I can act as a paid advisor of sorts. Maybe for £100 a month I can offer a 1 hour call, email support, and some accountability? Something along those lines – I haven’t really thought about pricing. Not hugely scalable, but there appears to be a bit of appetite for it, and I would be able to justify the time spent.

Like I say, this isn’t the most innovative bit of automation. It’s basically good template emails, a solid resources document, and a pro version of Calendly. But it makes my life SO much simpler, and easier to justify spending one hour a day helping other entrepreneurs.

I’d love to hear of ways in which you think I could improve or further streamline….

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