#36 JooBee's newsletter

TL;DR

🫥 Old Guard vs. New Guard? The hidden threat to scaling start-ups

🧩 My #1 tip for succeeding as the new guard

❓ Your views on OGs and NGs together to work cohesively

This newsletter edition is brought to you by Waggle 💛

Old Guard vs. New Guard? The hidden threat to scaling start-ups

When your start-up progresses from the ‘STARTing to build’ to ‘BUILDing to scale’ phase, it’s inevitable that you’ll bring in new leaders with the specific skill sets and experiences needed for this new phase. 

As much as you might hope for instant connection and cohesion, we humans are a tad more complex than that. Now, you've got two groups of leaders: the OGs (Old Guards), who've been with you since the beginning, helping your start-up grow from a tiny seed of an idea to finding its product market fit, and the NGs (New Guards), fresh faces brought in to transform your start-up with their expertise.

At this juncture, if you fail to align your OGs and NGs with common future expectations, your start-up will quickly descend into an 'us' versus 'them' scenario, splitting your organisation into two camps.

Here’s how you, as founder or CEO, can stop that from happening. 

🗞️ Old Guards feeling like old news

When shiny new leaders join, they’re brimming with ideas and it’s natural for you to be eager for them to inject fresh perspectives to take your business to the next phase. However, your OGs, who’ve been with the company since its inception, will start to feel undervalued or worse, uncertain about their future within the organisation as they see new leaders waltz in,  implement changes and replace old processes, systems and ways of working.

If this new vision isn’t effectively communicated to your OGs, it can feel as though their lifetime of work is being dismantled to make way for something entirely different. 

Feeling threatened, your OGs will likely cling to the past — the good old days — and may resist change. You might hear sentiments such as:

• “When we were 10 people, we used to….”

• “This isn’t how we do things around here”

• “They don’t get our culture”

👟 New Guards feeling like the shoes don’t fit

On the flip side, your NGs may feel threatened by the close bond your OGs have with you. While your NGs are doing their best to implement the changes you envisioned, they can’t help but notice that the OGs could just give you a call, complaining about the changes or the new kid on the block. Occasionally, you might even halt new initiatives out of concern for upsetting the OGs.

Feeling this threat and eager to make their mark, your NGs may overcompensate by citing their past experience and success to assert their value. You might hear things like:

• “When I was at ABC company, this is how we did it”

• “I’ve done this at X company and this works”

• “When I’ve done that, we succeeded in achieving [insert results]”

But underneath the bravado, there's a sense of insecurity, a worry that they'll never quite fit in with the established order.

Unite your OGs and NGs around a shared vision for the future

To avoid devolving into an 'us' versus 'them' scenario, as a founder, it's your responsibility to manage this change and communicate the business transformation that the collective leadership will undertake. 

Clarify the current situation and envision the future. For instance: “In the last few years, our business needed to operate in an agile manner, swiftly responding to customer feedback to build the right product for our market. Now that we have achieved product-market fit, our operations are evolving. We need to implement repeatable processes, systems, and practices to achieve consistent results as we take the product to a broader market.”

When you paint a clear picture of the future, it brings your OGs and NGs together, ensuring they're all on the same page instead of pulling in different directions. 

1️⃣Old Guards: Show them the opportunities and recognition

This transition also presents an opportunity for your OGs to learn from leaders with different experiences — a route to personal and professional growth. It’s important to show recognition of the immense contribution your OGs have made in getting the business to where it stands today. For example, in their 121s, take time to remind them that their deep contextual understanding of the business and customers is an invaluable asset and when combined with the experience of NGs, can ensure the continuous growth of the business. While it might be tempting to ’appease’ their concerns with a big job title or salary increase, this is a bad idea if they have not yet performed to the expected level. 

2️⃣ New Guards: Help them leverage the past and avoid ‘lift-and-shift’

As your NGs aim to leave their mark, it’s important to guide them to approach this transition with humility and a willingness to learn from those who have been part of building the company; this also helps them to build relationships. While their experience is valuable, it’s important to steer away from a 'lift-and-shift' mentality. Encourage them to blend the company’s unique history with their own past experiences to craft something unique and best suited for your business.

Transitioning your start-up from 'STARTing to build' to 'BUILDing to scale' is akin to blending seasoned veterans with fresh recruits on a winning team. Founders must lead like coaches, fostering unity and purpose. OGs mentor, NGs blend tradition with new ideas. Only as one team can your start-up level up successfully.

My #1 tip for succeeding as the New Guard

I typically join start-ups at the BUILD-to-scale stage, just after they’ve secured their Series A or B funding. This is my sweet spot—a critical pivot point where businesses must transition from creative chaos to a more structured, scalable approach that drives effective revenue growth.

I was the ‘New Guard’ 

When I come on board, I’m often joining alongside other new hires brought in to fuel the company’s growth and scale its operations. However, with growth comes inevitable change—and meaningful change requires buy-in. This buy-in cannot come solely from the founder or senior leadership team (SLT); it must extend across every employee in the organisation.

That’s why, whenever I start a new role, I’m acutely aware of my position as the New Guard (NG). I know my first priority is to connect, especially with the Old Guards (OGs). So, I prioritise one critical activity: meeting with every single individual in the company within my first three months (wherever possible).

Why 1:1s are my non-negotiable

Yes, meeting everyone takes time—a lot of it! And yes, I’ll be juggling projects and delivering results simultaneously. But I never compromise on those 1:1s, because they’re vital to my HR team’s success and the success of the business.

The goals for me are:

1. Understand what drives people & success: I need to know what our people value, what motivates them, and what they’ve contributed to making the company successful to date. It’s about capturing the DNA–and scaling it!

2. Introduce myself beyond the title: I want people to know me, not just as the Chief People Officer, but as JooBee—the person behind the role. Building trust starts with being authentic and approachable.

3. Set expectations for change: These meetings are an opportunity to gather feedback, share my vision and start conversations about how we’ll navigate change together.

Each insight gathered informs the way my team and I approach change. The more I know about our people, the better my team and I can design strategies that work for our business and the individuals driving it.

A fun puzzle piece memory 

One of the start-ups I joined didn’t just have an amazing culture—it had a playful and fun energy, too. As someone who loves preserving memories, I decided to buy a jigsaw puzzle. After each 1:1, I’d ask the person I met to sign their name and the date on one of the puzzle pieces.

What began as a simple personal keepsake turned into something deeply meaningful. Little did I know I’d one day share it with you in this newsletter, hoping to inspire you. 

When you join a new company and start building relationships with the people who will be part of the change journey with you, why not make it memorable—and fun? 🤸🏻‍♀️

Growth succeeds when NGs and OGs build strong relationships

Being the ‘New Guard’ can be tough––you are expected to bring change, drive performance and revenue growth. Success relies on building strong relationships with the OGs—the ones who laid the groundwork for the very opportunities you’ve stepped into.

Resist the temptation to ‘copy-and-paste’ strategies that worked in your last company. To deliver real results, you need to adapt your experience and expertise to the unique dynamics of your new organisation. Take the time to connect with the OGs: listen, learn, and collaborate. They’ll be instrumental in helping you scale the business effectively. By investing in these relationships, you’ll be better equipped to craft solutions that aren’t just effective but deeply aligned with your new environment.

And while you’re at it, don’t forget to create your own memories. 🧩 When you reflect on the journey, these moments will remind you of the people who shaped it—and why every challenge was worth it.

Need support to build your start-up to scale?

Here are 3 ways I can help you:

🔗 LinkedIn | 🌎 JooBee’s blog | 🤝 Work with me