door handle. Text: Questions from long-term leaders. logos: Pears Foundation and Leading in uncertainty with IVAR.

How do I know if I’m staying too long?

Questions from long-term charity leaders

This series shares some of the challenges 12 long-term leaders have been exploring together over the past 18 months, in regular sessions facilitated by our co-founder Director (and long-term leader himself) Ben Cairns. Convened by Pears Foundation, most of the group have been in their senior leadership post for 10 years or more, and many are also founders, or were instrumental to the founding of, their organisation.

The group started meeting before the Covid-19 pandemic, and then continued remotely, so their discussions spanned both pre- and post-Covid contexts. And while this series explores questions that were raised by long-term leaders, we believe that many of their considerations will resonate with all social sector leaders and professionals.

This blog series forms part of our work on Leading in uncertainty.


How do I know if I’m staying too long?

This question (and the associated ‘Who will tell me if I’m staying too long?) is one that many of us can identify with. But the flipside – ‘Why is there a sense of apology for being in the same role for over 10 years?’ – is more specific to long-term leadership.

For long-term leaders, it’s important to ‘continue to think expansively and innovatively about your organisation and your role’. The trouble is, the opportunity to do this – in a safe space, without undue pressure on the answer (i.e. the binary choice of staying or going) – is limited. Moreover, it may not be as simple as deciding whether to ‘stay or go’ – there could be a middle path that feels right to you.

So, with 12 long-term leaders coming together for the first time, it’s no surprise that this was the question on their minds. In exploring possible answers, we drew out some features of long-term leadership that may help with working out what’s right for your situation. They are both reasons for staying (assets which bring value to the organisation) and reasons for going (habits and dynamics that can hold others back).

Some features of long-term leadership

  1.  Institutional memory: ‘Knowing the intimate nuts and bolts of the machine helps you as a leader and as a decision maker’. However, this can hamper the ability of newer team members to be ambitious in their roles: it seems important to step back and allow people to find their own voice and perspective.
  2. Risk-taking: Does a long-standing leader’s deep knowledge of the organisation enable or inhibit its ability and drive to take greater risks: ‘I don’t want it to go bust on my watch’. The dangers of using ‘risk-taking’ as a ‘strategy to keep you motivated’ were also discussed: ‘A strategy that’s driven more by your own needs rather than the organisation’s needs’.
  3. Sustained relationships: ‘Building stronger, deeper, more authentic relationships over the long-term’, both internally and externally. Trusting relationships are often strengthened over time and ‘come into their own in challenging times of crisis … I can pick up the phone’. However, there are conflicting ‘push and pull factors’ and possible disadvantages in relying on length of service within an organisation, such as being overly dependent on one channel of relationships: ‘How can benefit from this longevity but without the organisation being overly reliant on one individual?’.

What might help?

What might help to mitigate the negative potential of these features, and enhance their benefits?

An exercise that has helped some leaders to stay motivated and conscious of an exit plan is to ‘spend time identifying your own drivers and long-term career aspirations and then, from this, relate it to your current organisation. This helps to create an exit strategy … framed by what does success look like to me in this role and when will it then be time to move on?’. Another approach is to be open to both the risks and virtues of being a long-term leader and engage openly and regularly with the staff and board about this: ‘whatever your plan ends up being, this thing needs naming and bringing out of the shadows’.


Are you leading in uncertainty?

Join us for some time to pause, reflect and share, connecting with other charity leaders who are adapting to and coping with prolonged uncertainty.
We provide  free and facilitated peer support sessions for voluntary and community sector leaders to share what’s front of mind in the current context of sustained uncertainty. During these online sessions, we are listening – so we can learn about and make sense of the live challenges leaders are facing, and help funders to understand how they can best respond.
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