Pancake series: 🥞 7 strategies to make scaling less painful, Part #2

Part 2

7️⃣ Strategies to make scaling less painful

The upgrading process and growth pains are inevitable, but how to make it all more bearable when “old and new” collide? We have some tips that we wish we had known before we started scaling and making the same communication mistakes.

1️⃣ Visualize the organizational structure early on

It will be helpful for your early employees if, from day one, you both do and communicate the following: a clear picture of the organizational structure. You should do that by answering the questions such as:

1. How will the company look if we grow and raise Series C? Why?
2. Which roles are tied to specific business/ARR goals? Why?

It’s important to approach this in reverse, and you can start by envisioning how the organization will look in 12 months. Folks will realize that the founder can’t have 40 direct reports anymore, as that is not scalable. They’ll also understand that they may have a Chief Product Officer who has already taken a company from Series A to C and will be effective in managing them in the future if we aim to grow quickly.

2️⃣ Beware of job titles

Titles can be particularly challenging in an early, growing company, where you may find yourself increasingly engaged in a game of title Tetris just to maintain everyone’s satisfaction. Soon enough, you might have seven VPs in a 25-person company — does that truly make sense? And when scaling up and introducing a new layer, is it truly necessary to bring in an SVP for the now 26-person company? However, when engaging with external partners or customers, it’s essential to clearly present your scope of responsibilities in the absence of titles. That’s what I appreciate about the approach of our founders at Deepnote; they didn’t care about titles, but if you need them to secure a customer or a candidate, go for it externally. Stripe had the same philosophy.

3️⃣ Use analogies for clear communication and open multiple channels

Discussing the future of the company openly using analogies can help junior and hungry employees. This will help them to visualize how the future may look like, to prepare for it and to make the transition smoother.

Acknowledge that different individuals excel in different contexts and roles. Some folks are great at building scrappy things and doing everything rather than following processes and executing in later stages. They specialize in a tiny little area of expertise. Some folks are great managers but struggle to navigate managers of managers. And that’s okay. You can’t be an A player in all contexts in the world, but it’s good to know what your sweet spot is.

Use all communication channels to openly discuss the challenges of scaling. All hands meetings or open door hours work well for a CEO, but this should be a team effort. Have all the experienced managers and/or more senior executives talk about it to their teams.

Share readings and resources on how other successful companies have navigated the scaling process.

4️⃣ Strength tests and individual specialization

Recognize that individuals have unique strengths and weaknesses. You can do that through strength tests, such as Gallup. That will help you identify and leverage team members’ strengths.

Emphasize the importance of knowing one’s sweet spot in contributing to the company’s success. It is also a job of a great manager to find the right “job” for a player. Someone may be a great goalkeeper, another one a striker, or a left-back. The team needs all of them‼️

5️⃣ Celebrate success and unique opportunities

Highlight that being part of the 10% of successful startups is a unique opportunity. Most companies fail. Emphasize that scaling represents success and a chance to build something special. Frame the scaling process as a once-in-a-life time opportunity for personal and professional growth

6️⃣ Reading club and live candid discussions

Organize a reading club to facilitate open discussions on scaling challenges. You can then organize a reading club as another platform to have an open discussion about it, inviting investors and guests who have been there and experienced this to talk about it too. We usually invited folks from our investors or other startups to all hands and discussed this topic very candidly, and that was amazing. We also had a founder who had to hire a CEO and discussed how he dealt with the changes, etc..We had a CTO who transitioned back to an individual contributor role, and he was thrilled that he could learn from a more experienced people leader.

You can also invite investors and experienced guests to share insights and experiences and foster candid discussions during all-hands meetings, bringing in founders and leaders who have faced scaling issues.

7️⃣ Recommended resources that we personally found helpful

1. Book: “Scaling People” by Claire Hughes Johnson. I am just reading it based on Milan’s recommendation and I am constantly asking myself why I haven’t found this book any earlier. Totally reflects all the scaling pains.
2. Podcast: “All Hands” — Episode Link Talks about how layering hurts everyone’s ego but it’s just so helpful to do that because you can gain so much.
3. Podcast: “Hiring Game Changers” — Episode Link How to scale by my favorite Maddy Cross.

And accept that no matter how much you communicate, there will always be friction, you cannot please everyone. Remember, navigating the challenges of scaling a company can be a very difficult task, but adopting strategic approaches can make the process less painful! 🤕