Navigating legacy power structures: turning old timers into allies

The weight of history

Every organisation has people whose influence isn’t tied to their current title, budget, or reporting line. Their power comes from something that can’t be bought, something much less visible, and something equally as potent: legacy

These are the people who have been there through multiple restructures, leadership changes, and strategic pivots. They know the “real” history. The unwritten rules, where the bodies are buried, and the reason why certain governance processes and policies we see as hinderances still shape decisions today. They may not sit at the head of the table, but they can sure sway the conversation in ways that surprise even the most senior and seasoned leaders

If you ignore them, you risk walking into traps you didn’t know existed. If you engage with them wisely, you can turn old timers into allies whilst everyone else naively dismisses them

Why legacy power matters

Those with legacy power often:

  • guard the culture. They see themselves as the custodians of “how we do things here” because they have seen so many people come and go. This is often seen as a risk mitigation or risk minimisation technique for them because they’ve done the time to figure out how to do things effectively over time and need to clean up the fallout of any changes that are made by the “new, young, and enthusiastic folks who don’t know what it’s really like”

  • hold institutional memory. They remember why certain decisions were made, and why other decisions failed and had to be rolled back

  • influence informally. Their opinion carries weight in the corridors, during coffee chats, and in conversations behind closed doors. They tell it like it is and they usually have good reason to hold the opinions that they do

This influence can work for you or against you. The difference lies in how you engage with it

The risk of misreading legacy power

Many product and transformation leaders make one of two mistakes:

  • overlooking old timers entirely. They dismiss them and mislabel them as resistant when all they want to do is help. They can see decisions are being made without the full set of information and are trying to shine a spotlight on the gaps. Treating them as “background noise” because they’re not in the formal decision making process is a mistake

  • challenging them head on. Trying to “prove” their way is outdated without understanding what they’re trying to protect is a mistake

Both approaches are common and are equally likely to backfire on you if you engage in this way. Overlooking them means you miss out on valuable context an potential allies. Challenging them without insight can trigger resistance that spreads quietly but effectively

Add more depth to your political landscape map

Last week we talked about mapping out the political landscape and leveraging what you learn to create a competitive advantage. Get that map out and look for:

  • those with long tenure

  • those who have survived multiple restructures

  • those with deep networks across different functions and departments within the organisation

  • those who have a reputation for “knowing how things really work in this place”

Stuck? Ask a trusted colleague: “Who do people listen to, even if they’re not in the room?”

I know who they are, now what?

Legacy power is rooted in history. To work with it, you need to understand:

  • what they’ve seen. The major wins, the painful losses, and the cultural shifts

  • what they value. Is it stability? Is it innovation? Is it recognition?

  • what they fear. Is it a loss of influence? Is it repeating past mistakes?

This isn’t about interrogating them for this information and then never speaking to them again. That would have the opposite effect to what you desire. It’s about showing curiosity. Invite them out for a coffee. Ask about their perspective on the organisation’s journey. Listen more than you speak

Then find some common ground. Once you understand their story, look for overlaps between their priorities and yours:

  • if they value stability, frame your initiative as a way to strengthen the organisation’s foundations

  • if they care about recognition, find ways to publicly acknowledge their contributions

  • if they fear repeating past mistakes, show how your approach avoids those pitfalls they can see a mile away

But beware. What they want to see is follow through. Don’t make the mistake of promising the world and not delivering on any of it. You only have one chance to turn old timers into allies. Don’t waste it by proving them right; by showing them that you’re just another new kid, enthusiastically trying to change the world, but destroys it in the process by asking for their feedback then discarding it thinking you know better

Once you’ve spoken to them, give them a role. People resist what they feel excluded from. That’s natural human behaviour. Involve legacy holders in the shaping of your initiative:

  • invite them to feedback and advisory sessions

  • ask them for their input on potential risks

  • give them visible credit for ideas they contribute

This doesn’t mean you hand over control to them. It simply means giving them a stake in the outcome

Finally, watch for the shifts in power and influence. Legacy power isn’t static. People retire, people move roles, and people have a right to change their minds. Keep your political landscape map updated. Notice when an old timer becomes an advocate, when they start to drift into neutrality, or when they cross over further into opposition

Example 1: Turning a skeptic into a sponsor

A General Manager in Transformation inherited a program that had stalled. One of the loudest critics was a long tenured operations manager who had seen three similar initiatives fail during their time at the organisation. They couldn’t see how this one was different and why it would succeed this time

Instead of sidelining him, the General Manager invited him to co-facilitate a risk assessment workshop. His deep knowledge of past failures helped the team avoid repeating the mistakes of the past. Within months, he became one of the program’s most vocal supporters, and his endorsement bought others on board because the others knew he wouldn’t be jumping on the bandwagon if he didn’t truly believe it would succeeed

Example 2: The guardian of culture

A Chief Product Officer underestimated a long tenured HR manager who had survived five CEOs. She wasn’t on the executive team, but her opinion shaped how the executives and their employees perceived change. By deliberately engaging her, framing the initiative as being aligned with the company’s values that she had a strong hand in defining, and giving her a visible role, the Chief Product Officer turned a potential critic into a cultural ambassador

Example 3: The silent broker

A Chief Strategy and Transformation Officer ignored a legacy holder who had been sidelined in a restructure. Though no longer in a senior role, the legacy holder still had deep relationships across the business. Her quiet resistance slowed down the adoption of the Chief Strategy and Transformation Officer’s initiative. Only after acknowledging her history with the organisation and inviting her into the conversations did momentum return

The balance of respect and renewal

Navigating legacy power is about balance. Respect their history, but don’t be trapped by it. Engage the old timers, but don’t let them dictate the future

Common mistakes product and transformation leaders make when seeking this balance include:

  • assuming old timers are always blockers

  • trying to “win” against them instead of engaging with them

  • ignoring the symbolic value of their support

  • over relying on them. Their influence is real, but not absolute

Once you’ve built trust with legacy holders, you can:

  • ask them to mentor emerging leaders, spreading their institutional knowledge in healthy and constructive ways

  • enlist them as change ambassadors. Their endorsement can legitimise new initiatives

  • document their insights. Capture valuable history before it’s lost

Handled well, old timers can become powerful allies in embedding change. The best product and transformation leaders honour the past whilst building for the future. They use legacy power as a bridge, and they don’t see it as a barrier

Your homework for this week

Who in your organisation holds legacy power? How could you turn their history into an asset rather than a hurdle?

Things you could do to help you with this:

  • identify one legacy power holder in your organisation

  • schedule a conversation to learn their story

  • find one way to involve them in shaping your current initiative

  • track how their stance shifts over time

Why this matters

Legacy power is one of the most underestimated forces in organisations. Ignore it, and you risk resistance you can’t explain. Engage it, and you gain allies who can accelerate your agenda and legitimise your leadership

The product and transformation leaders who thrive aren’t those who bulldoze the past. They’re the ones who turn history into an ally

Want help turning old timers with rich history and legacy into powerful allies?

Let’s work on this together. Here are three ways:

  • Influencing for Impact: This practical 2-day workshop is for you if you want to influence a decision maker, influence a change in customer or colleague behaviour, or influence someone to buy something from you

  • Executive and Leadership Team Coaching: Work directly with Lai-Ling to problem solve for your specific situation in a confidential setting. This is for you if you want to develop and execute on a game plan that is 100% tailored to you

  • Leadership Development: Invest in the product and transformation leaders in your company with leadership development that is customised for their role. This is for you if you want your people to learn about people and politics

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The hidden politics of restructures: reading between the lines