When Good Relationships Get in the Way of Good Leadership
Strong relationships can create alignment, but they can also hide weak operating design and make necessary challenge harder.
Great cross-functional relationships hiding weak org design?
YouTubeThis article is inspired by real workplace and leadership experiences. I do not use real names, company names or identifying details. Roles, teams, organisational structures, projects and business context may be removed, generalised or combined to protect the people and organisations involved while preserving the underlying leadership reflection. Where conversations are referenced, wording may be edited for clarity and anonymity.
The starting point
For several years, I thought I had a very good example of cross-functional leadership.
The relationship was between a pre-sales team and a post-sales team. Earlier in the organisation's evolution, those groups had effectively grown from the same broader team before separating into different parts of the customer journey. One focused on shaping the opportunity before the sale; the other took responsibility once the customer had moved into delivery and adoption.
Because many of the original people had worked together before that split, the relationship between the teams remained unusually close. We knew each other's strengths, understood the pressures on both sides, and had a shared sense of what good looked like across the customer journey.
As the teams grew, some of those original people became leaders. The relationships came with us, and that familiarity flowed into how the teams operated.
People spoke regularly. Work moved across the boundary relatively easily. There were recurring conversations about what we were seeing and where things needed to improve. If something became difficult, there was usually somebody on the other side who could be called directly.
At the time, I interpreted that as strong organisational alignment.
Looking back, I am no longer sure that was the whole story.
Some years later, after people had changed roles and new leaders had taken over, I found myself working with those areas again. I expected the relationship to have evolved, but I was surprised by how much of it had disappeared.
People who should have been closely connected barely understood what the other group was doing.
The regular exchange of context had gone. Some of the natural collaboration had gone with it. Responsibilities that once seemed obvious were no longer obvious at all.
My first reaction was probably the predictable one: how did we allow this to happen?
Then I started wondering whether that was the wrong question.
Perhaps we had never built as much structural alignment as I thought we had.
Perhaps we had built excellent relationships.
When relationships compensate for the system
There is an important difference between the two.
If two leaders know each other well, trust each other's intent and have enough history together, they can compensate for a surprising amount of organisational ambiguity.
They know who to call.
They can interpret something that was badly communicated because they understand the context behind it. They can negotiate a grey area without needing somebody to formally define ownership. If one team is stretched, the other may simply pick something up because everybody wants the overall outcome to succeed.
From inside that relationship, the system can feel very healthy.
Then those people leave.
Suddenly, the next group of leaders has to operate from what was actually designed rather than what their predecessors informally made work.
That was the first uncomfortable lesson for me.
Some of the alignment I had been proud of was probably more person-dependent than I realised.
But a newer relationship with another leader pushed the reflection further.
They came into their area without the history the rest of us carried. That meant they were willing to question some things that had become normal.
Why was their team doing only this part of the work?
Why could they not develop capability further upstream?
Why did another group automatically become involved in certain activities?
Were those boundaries intentional, or had they simply evolved because somebody on another team happened to be good at the work?
I agreed with many of the questions.
What made them interesting was that, historically, I am not sure we had asked them forcefully enough.
The existing model worked. Our teams had a good relationship. If one side needed something and the other side could provide it, we found a way to make it happen.
That felt collaborative.
It may also have reduced the pressure on each team to ask whether it was developing the right capabilities itself.
That is a much less comfortable interpretation.
Collaboration can become accommodation
Strong professional relationships are usually treated as an uncomplicated good, particularly in leadership.
And mostly they are.
I would much rather work in an organisation where leaders trust and respect one another than one where every boundary becomes territorial.
But respect introduces its own bias.
When you genuinely like another leader, understand their pressures and want them to succeed, you naturally become more willing to help. You make trade-offs. You accept some inconvenience because there is a bigger relationship to protect.
At what point does that stop being collaboration and become accommodation?
I do not think there is a clean answer.
There will always be moments where doing something slightly outside your team's theoretical remit is obviously the right thing for the wider business. Drawing perfect organisational boundaries is neither realistic nor desirable.
The problem comes when the exception becomes the operating model and nobody revisits why.
If my team continuously absorbs something because we can do it well, I may be helping a colleague while inadvertently preventing their team from developing the capability themselves.
If another leader consistently compensates for a weakness in my area, I might experience that as great partnership without recognising the dependency it has created.
And if the relationship is strong enough, neither of us may feel much pressure to challenge it.
The work gets done.
That is usually where leaders stop looking.
What are we protecting?
The question I have started asking myself is not whether relationships influence leadership decisions. Of course they do. We are human beings, not neutral components in an operating model.
The better question is whether I can recognise when that influence is becoming too strong.
If I avoid pushing another leader on something, am I doing it because the issue genuinely does not matter, or because I value the relationship and do not want unnecessary tension?
If I agree to my team taking something on, is that the right deployment of our capability, or is it easier than having the conversation about why another team is not doing it?
If a colleague challenges the model we have built together, do I defend it because it is objectively sound, or because I helped build it?
Those are difficult distinctions to make in real time.
It is also why I have become more interested in friction.
Not all friction is bad.
Sometimes friction is the evidence that a boundary is finally being examined properly.
A new leader asking why things are done a particular way can feel disruptive to people who have spent years making that system work. But the absence of historical relationships also gives them something valuable: they are less invested in preserving the compromises that came before them.
That does not automatically make them right.
They may lack context. They may underestimate why a particular arrangement evolved. Some of the things that look irrational from the outside may have very good reasons behind them.
But the question itself is valuable.
And good relationships should be capable of surviving it.
Respect should make candour easier, not harder
This is probably the part I have changed my mind about most.
I used to think one sign of a strong leadership relationship was how easily two people could align.
Now I think part of the test is how safely they can misalign.
Can I tell someone I respect that I think the way our teams are working no longer makes sense?
Can they tell me that my team has taken ownership of something it should not own?
Can one of us challenge a responsibility, decision or assumption without the other interpreting the challenge as an attack on the relationship?
If we cannot, then perhaps the relationship is not as strong as it looks.
There is also an obligation to the people we lead.
My desire to maintain a comfortable relationship with another leader should not quietly create a burden for my team that I would otherwise challenge.
Equally, fighting aggressively for every perceived team boundary is not good leadership either. Protecting your team can become its own kind of dysfunction if every discussion turns into a negotiation over territory.
The difficulty is holding both ideas at once: I should care deeply about relationships across the organisation, while still being prepared to create tension inside those relationships when the work requires it.
That is not something I think can be solved with a rule.
It is more of a diagnostic.
When an arrangement has existed for a long time, especially one built by people who get along well, I want to examine it occasionally as though those relationships did not exist.
Would we design it this way today?
Does each team own the capability it should own?
Are we collaborating because collaboration genuinely creates a better outcome, or because historical relationships have made the current arrangement easy?
And if we changed the people tomorrow, would the system still work?
That last question is probably the one I missed before.
I had seen a group of people working together extremely well and concluded that we had built an aligned organisation.
What we may actually have built was a group of relationships strong enough to make an imperfect organisation work.
There is still something worth being proud of in that.
But they are not the same achievement.
And knowing the difference changes what I would try to build next time.
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