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Interviewing 100 people in 100 days to discover their problems

Last Monday, I started a new challenge to complete 100 discovery interviews in 100 days

My strengths currently lie in execution, but my abilities fall short when it comes to recognising problems worth solving, this part of me has become blunt with years of putting solutions over the problems they're solving.

So over the next 100 days I'm going to try rewire myself to discover problems instead of solutions by interviewing 100 different people across a multitude of industries.

How it works

100 day challenges are fantastic when I have one straightforward input that I can do every day and measure it.

But interviews are not as straightforward, somedays I might not necessarily have an interview other days I might have more than one... Therefore the challenge by itself is currently an output metric and I'm not a fan of relying solely on output metrics, I think they're a terrible way to build habits and ultimately lead to almost certain failure because I'm not doing something productive towards the challenge each day.

To combat this I'm pairing the output metric of 100 interviews with an input metric of reaching out to 3 prospective people each day. That means each day the main thing I need to do is reach out to 3 people to hopefully line up a backlog of interviews.

By the end of the challenge, I will have reached out to at least 300 different people, with at least 100 of them turning into interviews.

After my first week

  • I reached out to 23 people
  • 12 of which replied to my initial outreach
  • 10 of those are booked in for an interview
  • 2 Interviews have already been complete

Honestly, I'm proud of this first week, although I only interviewed 2 people so far, I learned a lot about myself and what it's going to take to complete this challenge over the next 13 weeks for example:

Outreach is always hard...even when it's warm

The first few days were brutal, the sheer thought of messaging 3 people froze me in my digital tracks and it would take an entire day of putting it off before I finally hit send on those messages.

After those first few days, I've started to get into a rhythm that has sped up the task from taking all day to taking less than 30 minutes.

That lead to my next learning...

Outreach messages need to have a clear ask

I originally was worried if I asked people to chat with them upfront up I ran the risk of frightening them off so this initial message (below) was designed to warm up the idea then ask if they wanted to schedule a time to chat.

Hey X,
[PERSONAL MESSAGE]
I’m doing a bit of research into the tools and software [THEIR INDUSTRY] are using. Just curious, have there been any tools you’ve been looking for over the last few months that you are having trouble finding for [THEIR COMPANY]?

As you can probably tell after my first 5 messages it became obvious that this was just confusing and I changed up the message as so:

Hey X,
[PERSONAL MESSAGE]
A bit of a random favor but I’ve set myself a challenge this quarter to chat with 100 interesting people from various industries to learn more about what they do, the tools, problems, and intricacies. Down the line, this research may inform a product/service but for now, I'd love to catch up and chat with you a bit more about your experience in [THEIR INDUSTRY]
Let me know if you're interested and have some time free over the next few weeks for a quick chat.

This message is much clearer on what the ask is and it also drastically cut down the time from initial message to booking an interview.

but speaking of time between outreach and interview...

The delay between outreach and interview is real

I definitely underestimated how far out these interviews would be booked vs my initial outreach date. Most people prefer to have at least 1 week between booking a meeting and actually having it.

Fortunately if I factor this into my planning I can figure out how many interviews I need to be booking each week:

  • There are 14.2 weeks in the next 100 days
  • Minus the first week that has just passed and the final week, we're left with ~12 weeks
  • Assuming it takes on the average 7 days between initial outreach and interview scheduled
  • I need to be book at least 8+ interviews per week to hit my target of 100 interviews in 100 days

So, If you're keen to be interviewed! let me know!

I'll keep sharing updates on here and my blog (ryanwalker.blog) about the journey.

on January 23, 2024