Managing a Struggling Boss

managing up political minefield Feb 27, 2025

Navigating the Political Minefield: Managing Up When Your Boss Is Stuck

We often hear about the importance of managing our teams, but how much thought do we give to "managing up"—cultivating a productive relationship with our boss?

The truth is, a strong boss-subordinate connection is vital for your success and the health and productivity of the entire organisation.

This is especially important when your boss themselves is struggling to make the transition to the next step in the leadership pipeline and, as a result, exhibiting less-than-ideal behaviours. 

In this post, we explore the principles of "managing up," drawing from John P. Kotter's insights on power and influence. We also delve into a challenging scenario: what happens when your boss hasn't fully transitioned into their role, may be inadvertently impeding your progress, and is exhibiting questionable political behaviours? We connect these ideas to Ram Charan's work on the leadership pipeline and the political skills model of Baddeley and James (Donkeys, Foxes, Sheep, and Owls).

Why Managing Up Matters, Especially When the Politics Get Messy

In his work on 'Managing Superiors' Kotter explores bosses often significant formal power. Their support is vital for:

  • : Facilitating access to key networks and information.

  • : Advocating for the tools and support you need to succeed.

  • : Ensuring your work is in sync with organisational goals.

  • : Ensuring you are rewarded fairly for your contributions.

When these elements are lacking, your ability to lead and make a difference is severely hampered.

These are always essential, but they become critical when your boss isn't fully effective in their role and their political instincts kick into overdrive. 

The Pitfalls of Neglecting this Relationship

In his work Kotter* highlights the case of Frank Gibbons and Philip Bonnevie, which brings the need to manage upwards to life.

In short, Gibbons, despite being a "manufacturing genius," lacked people management skills. he was promoted to be a leader of leaders with Bonnevie in his team.

This created a challenging environment for Bonnevie, who had never before had to manage a difficult boss.

The failure to manage the relationship with the boss led to misunderstandings, poor coordination, and ultimately, significant financial losses for the company.

In the end despite doing all the 'right' things Bonnevie was fired.

Bonnevie had never had a "bad" boss before and didn't realise that it was his responsibility to manage the relationship. The cost to the company and the high personal price paid by Bonnevie could have been avoided.

This underscores the importance of taking a proactive approach to building a productive working relationship with your boss.

To unpick this situation, we could use a number of established theories.  

Ram Charan's leadership pipeline emphasises the importance of developing new skills and letting go of old responsibilities at each new leadership role as we take on more responsibility.

When a leader fails to make this shift, their direct reports often bear the brunt.

This is highlighted by the Bonnevie case above. Gibbons was a great at techical stuff, then promoted to lead a fucntion. In this new role he was not clear of his new responsibilities, or unable to fully step up to the leadership and more general management aspects of the role. This had implications for the business, and his team, as previously successful Bonnevie discovered.

To add another layer, the situation can be further complicated when the boss's insecurity or frustration manifests in negative political behaviours, as described by Baddeley and James*.

The Political Skills Model (Baddeley & James):

  • Sheep: Passive, naïve, and doing the 'right' thing. They avoid conflict and rarely assert their own needs.

  • Donkeys: Stubborn, inflexible, and often use brute force to get their way. They lack subtlety and can be openly aggressive / inept.

  • Foxes: Cunning, manipulative, and prioritise their own self-interest (they are not good news for those who have not realised the political game they are in - who often show sheep like behaviours, for good reason!)

  • Owls: Politically savvy, but also ethical and principled. They understand power dynamics, but use their influence to build consensus, foster collaboration, and achieve organisational goals. (If you don't want to be a sheep you can be an owl and sleep at night).

When a boss is struggling to transition, they may exhibit:

  • Donkey Moves: Becoming overly controlling, resisting new ideas, or using their authority to stifle dissent. They may be clinging to old ways of doing things out of fear or insecurity.

  • Fox Moves: Taking credit for your work, undermining your credibility, or creating a climate of competition and distrust. They may be trying to protect their position or advance their own interests at your expense.

In these situations, "managing up" requires not just understanding your boss's needs, but also navigating the political landscape with wisdom and integrity. 

Being a "Sheep" is not an option. Naivety will only make you a target. 

You need to become an "Owl".

The Pitfalls: The Case of Gibbons and Bonnevie (Revisited...Again!)

As previously mentioned, and as a reminder of the stakes involved, Kotter highlights the case of Frank Gibbons and Philip Bonnevie, where a failure to manage the relationship with the boss led to misunderstandings, poor coordination, and ultimately, significant financial losses for the company and the subordinate being fired.

In the case of Gibbons and Bonnevie, it is also possible that Gibbons was struggling with aspects of the leadership pipeline himself AND acting like a Donkey.

The Four Pillars of a Successful (and Politically Savvy) Boss-Subordinate Relationship

When your boss is struggling to adapt to their new role and exhibiting questionable political behaviours, the four steps Kotter outlines become even more strategic:

Step Description Key Actions Strategic Considerations (When Your Boss Is Stuck and "Playing Politics")
1. Understand Your Boss

 

Learn about your boss's goals, pressures, strengths, weaknesses, and working style.

* Identify their key objectives and priorities.

* Observe their communication preferences (e.g., email, meetings, phone calls).

* Understand their decision-making process.

* Recognise their strengths and weaknesses.

Diagnose their political tendencies. 

Are they acting like a Donkey (overly controlling, inflexible) or a Fox (manipulative, self-serving)?

Understanding their approach is key to developing an effective counter-strategy.

2. Know Yourself

 

Be aware of your own needs, objectives, strengths, weaknesses, and personal style.

* Identify your own goals and priorities.

* Assess your communication style and preferences.

* Recognise your strengths and weaknesses.

* Understand how your style might interact with your boss's style.

 

Resist the temptation to become a "Fox" yourself. While it may be tempting to fight fire with fire, maintaining your integrity is crucial for long-term success and your own sense of self-worth.

3. Create a Fit

 

Use the information gathered to create a relationship that fits both your needs and styles and is characterised by clear, mutual expectations.

* Communicate your needs and expectations clearly.

* Adapt your style to complement your boss's style.

* Establish clear lines of communication.

* Discuss how you can best support your boss's goals.

Set clear boundaries. 

Assert your needs and expectations assertively, but respectfully.

Don't allow yourself to be exploited or manipulated. 

Focus on shared goals. 

Frame your requests and suggestions in terms of what benefits the organisation as a whole.

4. Maintain the Relationship

 

Keep your boss informed, behave dependably and honestly, and use their time and resources selectively.

* Provide regular updates on your progress.

* Be reliable and follow through on your commitments.

* Be honest and transparent in your communication.

* Respect your boss's time and avoid unnecessary requests.

* Escalate issues promptly and propose solutions.

Document everything meticulously. 

Keep a record of your accomplishments, communications, and any agreements you reach. This will protect you from potential misunderstandings or attempts to rewrite history.

 

Additional Strategies for Navigating a "Stuck" and Political Boss

  • Build Allies: Cultivate relationships with other key stakeholders in the organisation who can provide support and advocacy.

  • Seek Mentorship Elsewhere: Find a mentor or advisor outside your direct chain of command who can offer guidance and perspective.

  • Focus on Results (and Make Sure They're Visible): Consistently deliver high-quality work that aligns with organisational goals and make sure your contributions are recognised.

  • Manage Your Reputation: Maintain a professional demeanor and avoid getting drawn into office politics or gossip.

  • Know When to Walk Away: If the situation becomes toxic or unsustainable, and you've exhausted all other options, it may be time to consider other opportunities.

Final Thoughts

"Managing up" is always a delicate art, but it becomes a high-stakes game when your boss is struggling with their own transition in the leadership pipeline and resorting to negative political tactics. 

By understanding the dynamics at play, developing your own political savvy (channeling your inner "Owl"), and focusing on delivering results with integrity, you can navigate these challenges and continue to advance in your career—without compromising your values.

Remember, you have agency.

By proactively managing the relationship and protecting yourself from political manoeuvring, you can create a path for growth, even in the most challenging circumstances. Do not be a fox, but definitely do not be a sheep. 

Instead, be an owl.

ps Contact me if you want me to support your leaders to transition effectively into roles to avoid all this drama! 

If you want to read more:

*Kotter, John P. Power and Influence. New York: The Free Press, 1985. 

*Baddeley, A., & James, K. (1987). Politicking for Career Success: A Typology of Deviant Impression Management. Personnel Review16(7), 3-9.

*Charan, R., Drotter, S., & Noel, J. (2011). The Leadership Pipeline: How to Build the Leadership-Powered Company. Jossey-Bass

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