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How to effectively coach your boss

Ever wondered how to become the ‘Boss Whisperer’? Our Creative Director, Adam Goodman-Smith, explores the importance of coaching your boss, when it might be necessary, and provides five top tips for doing it effectively.

Coaching is a skill that is often associated with guiding, supporting and developing employees. It’s used to unlock a person’s potential to maximise their own performance, most commonly used in the workplace to set performance or personal development goals, career planning and taking on new tasks or projects.

However, my view is that there are situations where it’s not just your direct reports who require coaching, but your boss as well. Approaching this can be a delicate endeavour depending on how ‘big’ your relationship with your boss is. But when done right, it can lead to all sorts of benefits, namely increased trust, better communication, a more productive work environment, and even personal and professional growth for both you and your boss.

Looking back a few decades, it was common for leaders to adopt a command-and-control attitude, shutting themselves away in their office, isolating themselves from the rest of the team and making it difficult for employees to reach out to them.

What we’re seeing now is the shift away from that traditional model within the workplace, and instead a move towards adopting a flatter structure, where teams self-organise. In this context, the role of the leader, therefore, is less about command and control and more about galvanising team spirit/morale.

In this new world, where organisations are opting to curate and disband teams around projects (the agile approach) in which team members are drafted in based on knowledge and experience and ‘released’ after the project is completed – hierarchy becomes less important. As the levels are dismantled, it opens the doors for employees to step forward and offer assistance and insight and do so with confidence.

For some, the thought of coaching their boss might still be terrifying. For others, it might sound counterintuitive, as they are typically seen as the ones responsible for guiding and mentoring the team. Whatever your current situation or stance may be, here are some compelling reasons why you might want to give this a go.

The Benefits of Coaching Upwards

  1. Enhancing Communication: Effective communication is key in any working relationship. Coaching your boss can help improve their understanding of your perspective, leading to more open and honest dialogues.
  2. Promoting Professional Growth: Just like employees, leaders can benefit from personal and professional development. Coaching can help them become better leaders and decision-makers, benefiting the entire team.
  3. Building Trust: When you coach your boss, it shows that you are invested in the success of the team and the organisation. This can foster trust and strengthen the bond between you both
  4. Problem-Solving: Sometimes, your boss might be unaware of certain issues or roadblocks that you encounter. Coaching can help identify and address these problems, improving efficiency and productivity.
  5. Encouraging Adaptability: The workplace is constantly evolving. Coaching your boss can help them stay up to date with the latest trends and technologies, fostering adaptability and innovation.

So, now we have looked at the benefits coaching upwards can bring on both your boss, yourself, and the wider team, it’s important to know when to put it into practice.

Only you will know when the time is right to begin introducing coaching into your daily conversations with your boss. Choosing your moment is important. Here are a few scenarios where coaching your boss might be appropriate:

When to Coach Your Boss

  1. Performance Feedback: If you notice specific behaviours or practices in your boss that are hindering team performance, it’s an excellent time to offer constructive feedback. This could be “What was your intent in that situation?” or “Can I offer you my observations and thoughts on what went down?”
  2. Strategy and Planning: When you have insights or ideas that could benefit the organisation, don’t hesitate to discuss them with your boss during strategic planning sessions. For example, you could say “I’m wondering about X, and wondering if we could benefit from Y. What do you think?”
  3. Conflict Resolution: If there is tension or conflict within your team, your boss may not be aware of the full extent of the issue. Offering your perspective can help resolve the matter more effectively. A way to do this is by saying “Let me offer you another perspective…”
  4. Personal Development: If your boss expresses a desire to improve their leadership skills or asks for feedback, take this as an opportunity to engage in coaching. A way to approach the conversation could be “My experience of you is X. The impact this has on me is Y. What I need more or less from you is…”
  5. Major Organisational Changes: During times of change, such as mergers, reorganisations, or shifts in company culture, offering support and guidance can help your boss and the team navigate these transitions more smoothly. You could do this by saying: “What do you need more or less of from me right now?”

Hopefully by now you have a better understanding of what coaching upwards is, what the benefits are and what situations it can be used in. To truly become the ‘Boss Whisperer’, takes time and practice, and everyone’s circumstances will be different.

There are, however, specific coaching tips that you can take with you to make the experience a positive and productive one.

Here are five top tips that should be considered when you enter the practice:

Top Five Tips for Coaching Upwards

  1. Choose the Right Approach: Start by considering your boss’s personality and communication style. Some leaders may prefer direct, assertive feedback, while others may respond better to a more subtle, diplomatic approach. Tailor your coaching style to their preferences.
  2. Be Solution-Oriented: When offering feedback, focus on providing potential solutions rather than dwelling solely on problems. This demonstrates your commitment to helping your boss and the team overcome challenges.
  3. Stay Respectful and Professional: Maintain a respectful tone throughout the coaching process. Avoid criticising or blaming, and instead, emphasise the positive impact the changes could bring.
  4. Encourage Open Dialogue: Create a safe space for honest and open discussions. Let your boss know that you value their input and perspective as well. Effective coaching is a two-way street.
  5. Follow Up: After offering feedback or suggestions, follow up to see how the changes are progressing. Be prepared to offer ongoing support and further assistance as needed.

In conclusion, coaching your boss can be a powerful tool for personal and professional growth, as well as the success of the team and the organisation. It’s not about undermining authority but rather enhancing collaboration, communication, and problem-solving.

By choosing the right moments, employing effective coaching techniques, and maintaining professionalism, you can become a valuable asset in helping your boss become the best leader they can be. In doing so, you contribute to a more productive and harmonious work environment that benefits everyone involved. Give it a try and see where it takes you.

Article originally posted on Coaching at Work, read here.

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