[Leadership Nuggets] The Secret to Ultra-Fast Startup Growth

Since launching my first company over 7 years ago, I’ve had a lot of conversations with CEOs and startup founders about how to unlock rapid growth, whether it was for my company or theirs.

I’ve also advised some early-stage startups about their current growth strategy and approach to founder-led sales, and I even teach some startup lessons from time to time at the nearby university.

Here’s one tactic that I like to call my “secret to startup growth”.

TLDR:

• The goal: Generate rapid business growth
• The tactic: Set up 1-on-1s with everyone on the team
• The result: Launch a major feature every 30 days. Release daily product improvements. Create a content pipeline for near-daily social media and blog posts.

What is a 1:1 meeting?

“1:1s” are simply meetings between a manager and direct report. For example, I might have a 1:1 with my head of marketing, while my head of marketing would have a 1:1 with our content manager or digital marketing specialist.

What makes them different from typical day-to-day meetings is that there’s no set goal. 

Instead, a 1:1 is more like an open forum where you can discuss how the month has gone, whether there were any hurdles or challenges, and if the employee is feeling comfortable with their work, their colleagues, or the company in general.

Why are 1:1s important?

Because most startups are small (usually under 50 people), a lot of new and young workers tend to assume that 1:1s are more for large corporations and enterprises.

If anything, 1:1s are even more important for early-stage companies. One of my earliest startup lessons learned was the value of 1:1s for connecting with team members and fostering a positive company culture.

At both AiSDR and AXDRAFT, I’ve always tried to set up monthly 1:1s with my direct reports, as well as skip level meetings at the end of the month.

Here’s what I do.

Step 1: Schedule a 1:1 with every member of the team

At the time of writing, AiSDR has 18 people, including myself and my co-founder Oleg.

It’s easy for small teams to set up a 1:1 with every team member. But as the team scales, it gets harder. Once your team passes 50 people, it’s effectively impossible.

I’m fortunate enough to be able to split meetings with Oleg. He covers the product development team while I handle the sales, marketing, and customer success teams.

For each 1:1, I try to set aside 30-45 minutes. I find 15 minutes to be too short, if not rushed, and very rarely does a 1:1 meeting last one hour.

Step 2: Start off with a simple conversation to build a rapport

A 1:1 isn’t a pure business meeting. Rather, it should be treated as a chance to connect and bond.

This is why I always lead off with simple conversational questions. If I know a person’s an avid traveler, I might ask them about any recent or upcoming trips. Or if they’re always playing the latest video games, I may ask what they’re playing and how they like it.

One of my employees is almost like a walking encyclopedia. At one 1:1, we might find ourselves discussing a random topic like the American Revolution, then at the next 1:1, we’re diving into cultural linguistics and why the British start every conversation about the weather.

In the end, the first 5-10 minutes is just a simple chat to create a calm atmosphere and give a chance to relax from previous work tasks. 

Step 3: Gradually pivot the discussion to company matters

Once it’s time to shift the conversation to work, it’s important to do so gradually. This allows you to preserve the calm atmosphere you built at the start of the meeting. Otherwise, if you’re suddenly like, “Welp, that’s enough chitchat. Let’s talk about work”, this could undo any bonding by making it seem like your previous conversation lacked meaning.

At this point in the 1:1, I try to touch on several topics:

• How do they feel about their current responsibilities?
• Does the workload seem too heavy or too light?
• How are they getting along with their teammates?
• Were there any moments during the month that were especially hard?
• Was there anything they worked on that they really enjoyed?

As they answer, I try to practice active listening. I give them my full attention, I avoid interrupting them mid-sentence, and I attempt to understand their perspective.

If they have any questions, I try to respond honestly, and if they have concerns, I share my thoughts and advice.

The end goal here should be to remove any bottlenecks, eliminate misunderstandings, and create alignment.

Step 4: Share goals and future plans

I try to set aside the final 5-10 minutes to ask if the person has any goals, whether it’s in life, at the company, or in their career. This helps me understand how I can help them grow personally or professionally. (It’s also the perfect moment to check if they plan to go on vacation or take time off.)

Additionally, 1:1s are a good time to loop people in about the company’s future plans and how they fit. This helps keep them aligned with the company’s goal.

Step 5: End on a positive note

I like to finish up the meeting by thanking the person’s work during the month, and by reiterating my hope that the next month will go even better.

I also leave an open invitation that if they run into any issues, they don’t need to wait until the next 1:1. They can simply reach out to me at any time.

The Result

Regular check-ins are my secret startup growth strategy. Time and time again, they’ve helped unlock super-fast progress towards our goals.

Thanks to 1:1s, my team at AiSDR:

• Grew from “idea” to “business plan” to “MVP” to a fully launched product in less than a year.
• Ships a critical feature to production every month.
• Releases daily improvements to the product.
• Creates near-daily social media and blog posts, as well as a monthly newsletter and guide.