Less Annoying Business: How I ask questions in 1:1s that get honest answers

publishedabout 1 month ago
4 min read


Tyler from Less Annoying Business here. Here's what's new:

New content

The Trough of meeting overload [Blog post]
As LACRM has grown, I've found myself in more and more meetings. But recently, things actually seem to be trending in the opposite direction. I suspect this is something a lot of founders experience as the company becomes big enough to have teams with their own managers.

How I ask questions in 1:1s that get honest answers [Blog post]
I just had a round of 1:1 meetings with everyone at LACRM, so I figured I'd share my process. Yes, I see the irony in posting this immediately after the post about how I don't have as many meetings anymore.

Bullish or bearish: NFTs, location-adjusted remote pay, and startup studios [Podcast]
The new podcast I'm experimenting with is still private, but if you'd like to give it a listen you can get an invite here. We only recorded one episode this month, in which we discussed a few trending topics in the tech industry.

What I'm working on


Every six months, I go through a cycle that helps LACRM stay on track and align everyone behind common goals. I plan on writing a blog post about this soon, but for now, the basic structure looks something like this:

  • Meet with the leadership team to make important decisions, figure out important topics, set strategy, etc.
  • Present the main takeaways from the leadership team meeting to the rest of the company in an all-hands meeting.
  • Meet 1:1 with each employee to get their feedback (this is where I ask the questions mentioned in the blog post I linked to above).

I just finished that part of the cycle. It's a real grind. Lots of prep work goes into the presentation followed by 17 hour-long meetings over the course of less than a week.

I'll spend the next couple work days decompressing, and then I'll dive into addressing all of the ideas and issues that came out of the 1:1 meetings. This process results in major improvements for the business, but it's also one of the most draining parts of the job.

Product strategy

Normally in all-hands meetings I'll do a deep dive about a topic that's been on my mind. This time, it was about the long-term product strategy. We've been doing a lot of thinking and reflecting, and I think we have a more clear vision for the future of the LACRM product than ever before.

I won't bore you with all the nitty gritty details, but the summary is that because we don't want to complicate our core CRM product (our customers use us because we're simple), instead, we want to solve more problems for the same people. Ideally, these different solutions will work well together (I hate the word "synergy" so imagine I used a different word that means the same thing).

Here's what we're hoping to build over the next decade:

  • Contacts (we already have this this, it's what the CRM is)
  • Calendar (the CRM has a calendar, but it's not good enough to stand on its own yet)
  • Tasks (we have a task feature but it suuuuuuuucks so there's a lot of room for improvement)
  • Internal messaging (something like Slack, but we have some ideas on how to make it both simpler and more useful)
  • Notebooks (think Dropbox Paper or Notion, but for low-tech users)
  • Email (a client, not the actual hosting part)

Additionally, we're going to try to be more intentional about product-led growth so that we can have a more predictable and sustainable growth plan for the next decade and beyond.

As Dwight Eisenhower (and many other people) said: Plans are worthless, planning is everything. Nothing about the plan above will happen the way I described it in the all-hands meeting, but it's important to have a vision that we can all work towards. I'm excited to dive in.

Good stuff on the internet

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Shreyas Doshi
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October 12th 2021

I love this point. This might sound weird, but I think tech companies, especially indie hackers, have become almost cowardly when it comes to product decisions. People worship metrics and validation so much that they seem to forget that at the end of the day, we have to have original ideas and good intuition. Validating ideas is great, but you can't validate everything, so you need to have good instincts and taste.

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Angelina Fabbro
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September 30th 2021

This is great advice. One of the reasons we want to build a more complete calendar product is because I actually think our technology could be doing a lot more to help with this. Why is it that when I create an event on a calendar, there aren't fields specifically for these things (agenda, outcomes, etc.)? Even worse, why don't calendars have tools for creating the action items and meeting notes?

This can be solved with policy, but it'd be a lot better if the technology nudged people in the right direction.

My one quibble is that it's ok for meetings to exist for social reasons. I don't think it's a bad idea to have teams meet once per week just to catch up, look each other in the eye, and share a laugh or two. But if a meeting is about getting shit done, Angelina's approach works.


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