Enterprise Leadership · Organisational Design · 11 min read
When Going the Extra Mile Becomes the Operating Model
How repeated heroics can turn into structural dependency — and what managers can do before high performance becomes a career trap.
Going the extra mile is usually treated as a positive thing.
Someone stays longer to help resolve a difficult customer issue, steps into a conversation that technically belongs to another team because they know they can help, mentors a colleague without being asked or finds a better way of doing something that has frustrated everyone for years. Most organisations want people who behave this way, and most managers are understandably grateful when they have people on their teams who can be relied upon when things become difficult.
The problem begins when exceptional effort works so well that everyone gradually starts depending on it. The difficult customer goes to the same person because they know how to handle them. Technical questions gravitate towards the person who understands both the technology and the customer. New colleagues are sent to them because they are good at explaining things. When something falls between organisational boundaries, they are trusted to pick it up because everyone knows it will get done.
None of those decisions necessarily looks unreasonable on its own. In fact, many of them are signs of trust. The employee may enjoy the responsibility as well. Capable people often like difficult problems, enjoy helping others and take satisfaction from knowing they can make a difference. I certainly have. But over time, a series of sensible individual decisions can create something nobody deliberately designed: an operating model that quietly depends on one person doing far more than the role was ever intended to require.
When more responsibility really is development
There is nothing inherently wrong with giving strong performers more difficult work. In many careers, that is exactly how development is supposed to happen.
Technical Support provides a useful example. Someone may begin in first-line support dealing with relatively standard issues. As their knowledge and judgement develop, they start handling more difficult cases and may eventually move into second-line support. From there, they might progress into third-line or specialist support. The problems become more complex and expectations increase, but the progression is visible. The role changes, the compensation normally changes, the employee develops new skills and there is an organisational structure around what has happened. L1 is expected to escalate certain problems to L2, and L2 knows when specialist expertise is required.
In management, Customer Success and many broad enterprise roles, progression is not always as clear. Two people can hold exactly the same title while operating at very different levels of complexity. One might manage three relatively stable customers. Another might manage eight, including some of the most demanding accounts, while also mentoring colleagues, supporting escalations and becoming the person others call when technical or commercial situations become complicated. The title may remain identical and the salary band may remain identical, even though the contribution has changed substantially.
That is where development can gradually become a competence penalty. The person who repeatedly demonstrates greater capability is rewarded with greater responsibility, but the structures that normally accompany progression do not necessarily move with them. More difficult work is still valuable experience, and many people actively want it, but there comes a point where responsibility, recognition, authority and progression need to remain reasonably connected.
The capabilities that were never officially required
I have spent much of my career somewhere between management and technology. I have worked with excellent non-technical managers and excellent technical people who had little interest in management or customer-facing leadership. My own advantage was often that I had enough experience in both worlds to move comfortably between them.
In several roles, deep technical knowledge was never formally required. You could perform the job without understanding infrastructure, architecture, troubleshooting or implementation details at a particularly high level. Yet I learned over time that technical knowledge made many parts of the job easier to do well. It helped me ask better questions, recognise when something did not make sense, challenge assumptions, work more effectively with technical teams and speak credibly with customers when situations became complicated. It also made it easier to connect customer expectations, commercial commitments and technical reality without constantly needing somebody else to translate between them.
Those skills were often officially nice-to-haves. Operationally, they sometimes felt much closer to capabilities the role genuinely benefited from.
That creates an interesting problem for a manager because the obvious solution may not be available. A manager might recognise that people with a particular combination of technical ability, judgement and communication skills consistently perform better, while still having no practical way to redesign the role across the organisation. Retraining an entire workforce would be expensive and time-consuming. Changing global hiring criteria could require agreement far beyond one manager's authority. The organisation might also reasonably decide that not everyone performing the role needs the same technical depth.
The leadership problem is therefore not necessarily failing to redesign the organisation. Sometimes that simply is not realistic. The problem arises when the organisation benefits indefinitely from people who happen to bridge the gap without recognising that they are contributing something materially different.
There are several ways a manager can respond within the authority they do have. Additional responsibilities can sometimes be formalised through a Team Lead or specialist position, particularly when mentoring and training have become a meaningful part of someone's contribution. The employee may be ready for promotion into another role entirely. In larger organisations, adding a Senior designation or moving someone into a higher compensation band can sometimes recognise greater capability without requiring a completely different job. Workload can also be adjusted so that mentoring, enablement or specialist support become legitimate parts of the person's capacity rather than additional work layered on top of everything else.
None of these options will exist everywhere. What matters is recognising that doing nothing is also a choice.
How exceptional performance becomes structural dependency
The trap normally forms gradually. A difficult customer situation appears and the strongest person is asked to help. They resolve it, so the next difficult situation naturally finds its way to them as well. A colleague needs help understanding something technical, so they spend an hour explaining it. A reporting process is inefficient, so they improve it. Someone leaves and they cover an account temporarily. A new employee joins and they help them get up to speed because they know the environment better than almost anyone else.
Each action makes sense. The employee may even volunteer because solving the problem feels easier than watching it remain unresolved. That is one reason I don't think it is reasonable to blame the person going the extra mile for creating the dependency. If a customer is struggling and you know how to help, helping is often exactly the right thing to do. If a colleague needs knowledge you possess, sharing it is a positive behaviour. If a process is broken and you can improve it, most good organisations would hope that you do.
The leadership responsibility begins when those exceptions form a pattern. At some point, a manager should become curious about why the same person keeps appearing in the same situations. Why does this customer only seem to work effectively when one particular person becomes involved? Why is one employee carrying substantially more customer scope than peers with the same title? Why do new employees depend so heavily on them? Why is important knowledge concentrated in one place? Why has something that began as temporary assistance quietly become part of that person's permanent workload?
These are not criticisms of the employee. They are signals about the system around them.
Customer relationships can make the dependency particularly difficult to unwind. Someone who has repeatedly gone beyond the normal expectations of their role may accumulate years of customer history, technical knowledge and personal trust. They know why previous decisions were made, which internal teams can actually unblock particular issues, which stakeholders need early communication and which apparently technical problem may really be an issue of trust, ownership or alignment.
The customer understandably values that experience and may eventually start asking for the individual specifically. That is flattering, but it is also a warning sign. If the employee moves to another role and their replacement performs the job exactly as it was originally designed, the customer may still perceive a decline in service. They are not comparing the new person with the job description. They are comparing them with years of accumulated relationships, knowledge and discretionary effort.
At that point, the organisation can discover that part of what the customer believed was the company's service was actually one person's ability to compensate for gaps in the operating model.
When someone becomes too valuable to promote
This can eventually create one of the strangest consequences of high performance. The employee has demonstrated that they can operate beyond the expectations of their current role. They handle complexity well, customers trust them, colleagues learn from them and their judgement is relied upon. In almost every sense, those are signs that somebody should be developing towards greater responsibility.
Then an opportunity appears and the very things that demonstrate their readiness can become reasons not to move them. Who will take the customers? Who can replace their knowledge? Who will mentor the new people? What will happen to the difficult account? Who else understands all of the informal processes and relationships that have accumulated around them?
The organisation may genuinely value the employee and genuinely want to retain them while simultaneously having built so much dependency around their current position that progression becomes difficult. The person can then find themselves looking at colleagues with the same title and wondering why they are carrying more customers, solving more complicated problems, mentoring others and sharing improvements while someone else progresses first.
What originally felt like, we trust you because you are capable, can slowly begin to feel like, we give it to you because we know you will do it.
If somebody becomes too important to promote, I don't think the organisation has successfully retained talent. It has failed to manage dependency.
Managers cannot always prevent this entirely, and employees do have some responsibility for making additional work visible. A manager cannot respond to something they genuinely do not know about. But once the pattern is visible, simply continuing to benefit from it is not enough. Leadership should be thinking about documentation, succession, backup coverage, workload, knowledge transfer and development long before the employee announces that they want another role.
The employee may create the heroic workaround. Leadership decides whether the workaround remains temporary or quietly becomes the operating model.
Turning individual capability into team capability
One of the best managers I worked with approached this very differently.
We worked in a large technology organisation and usually recruited new people into our team from elsewhere inside the company. Support was a particularly good source of talent because we already knew many of the people there. We had seen their technical abilities and, just as importantly, had often seen how they communicated, collaborated and behaved under pressure.
When we needed another person, my manager would often ask me who I thought would be a good fit. He was not simply looking for someone who met the formal job description. He understood from experience that the strongest people in our team tended to combine technical credibility with communication skills, curiosity and the ability to build trust with customers. I knew people in Support who already demonstrated that combination, so he would ask for my opinion and sometimes ask me to encourage the people I recommended to apply.
When they joined the team, I helped mentor them as they learned the new role.
I did not really think about this as succession planning at the time. Looking back, that is partly what it achieved. My manager did not simply recognise that one person possessed a useful combination of capabilities and continue routing more work towards them. He asked what made that capability valuable and deliberately brought more people into the team who could develop in a similar direction.
They were not clones. Everyone brought different personalities, experiences and strengths. What changed was that technical credibility, customer judgement and the ability to bridge different parts of the organisation were no longer concentrated as heavily in one place. Knowledge spread, customers had more people they could trust, new employees developed faster and the team became more resilient.
My manager had not rewritten the organisation's global recruitment strategy. He had not retrained hundreds of employees or created an expensive new capability programme. He simply recognised what was helping his team succeed and used the influence available to him to build more of it.
That experience has stayed with me because it demonstrates an important difference between recognising a high performer and learning from one.
Recognition is only the beginning
I have written before about the importance of making invisible work visible. Managers should understand who is mentoring colleagues, preventing incidents, taking difficult customers, sharing knowledge and quietly solving problems before they ever become visible in executive dashboards. Recognition matters because people should know that meaningful contribution is noticed.
But recognition is only the beginning. Once a manager sees that contribution, the more important question becomes what they do with what they have learned. Telling somebody they are indispensable sounds complimentary until being indispensable prevents them from progressing. Thanking someone for continually going above and beyond sounds positive until going above and beyond becomes the expectation. Celebrating specialist knowledge is useful until nobody else is given the opportunity to acquire it.
The objective should never be to make exceptional people less valuable. It should be to turn some of their individual capability into organisational capability while continuing to develop and reward the person who helped create it.
The practical answer will differ between organisations. It might involve promotion, a Team Lead or specialist role, a Senior designation, higher compensation, reduced ordinary workload to make space for mentoring, deliberate knowledge transfer or recruiting people who bring similar complementary capabilities. A manager may not have authority over every one of those options, but they can make the dependency visible and use the influence they do have rather than waiting for a resignation or promotion request to expose the problem.
Going the extra mile will always have a place at work. Difficult situations sometimes require somebody to step beyond the normal boundaries of their role, and many of the best people I have worked with do that willingly. The leadership challenge is recognising when exceptional effort has stopped being exceptional.
Good leaders appreciate the people who repeatedly go the extra mile. Great leaders ask why it was necessary, understand what makes those people successful and build enough capability around them that the organisation no longer depends on them doing it every day.
I would genuinely be interested in how other managers approach this. When someone in your team becomes unusually valuable because of knowledge, relationships or capabilities that are difficult to replace, how do you continue developing that person without allowing the organisation to become dependent on them?
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