Managing Up, Part 5: Your Cheat Sheet and Guide to Boss Personas
Hello there, lovely product people! I wanted to share a quick note to let you know that this article is a little different from what I usually share here. While my blog typically highlights work I’ve already done (e.g. frameworks I’ve developed, podcasts or talks I’ve given, clients I’ve worked with), this post actually represents a work in progress. I’m in the midst of developing a talk and I wanted to share some of the content I’ve been working on. In other words, this is far from polished.
I hope sharing some of my thoughts here will help me refine what I’d like to say in my talk. And if you have any feedback on any of the content here—please don’t hesitate to let me know by sending me an email at info@petra-wille.de.
In the first post in this series, I covered why managing up is an important topic, introduced the ten boss responsibilities and the ships vs. shipyard metaphor, and explained why your boss might be struggling in these areas. Want to read that post? You can find it here. In the second post, we looked at a common situation product managers find themselves in: struggling to say no to different requests. We identified that this is linked to the boss competency of directional clarity and explored some ways you can help your boss develop in this area. You can read that post here. In the third post in the series, we explored what you can do when you’re experiencing conflict with other people or teams. Read that post here. And in the fourth post, we explored the topic of professional development and how you can make sure your boss helps you become the best PM you can be. Find that post here.
In this post, the final in the series, we’ll be reviewing the most important points for you to remember (I’m calling this your “Managing up cheat sheet”) as well as some ways to make sure you tailor your message to your manager’s communication style.
Managing up cheat sheet
Throughout the past few posts, we’ve looked at some common challenges you might face with your manager and how to overcome them. Now here are some tips to keep in mind as you try to put those ideas into practice.
Make sure you know what you can rightfully expect from a product leader. In the first post in this series, I mentioned the ten boss competencies: Directional clarity, Process oversight, Cultural advocacy, Role clarity and ownership, Development facilitation, Networking support and conflict management, Empowerment through trust and autonomy, Feedback culture and recognition, Resource enablement, and Integrity and ethical leadership. Keep that list somewhere close as it will help you to give feedback to your boss on the spot.
Make sure you learn a thing or two about your boss to tailor your messages:
How do they see their role?
How do they think they are adding value to the company in their role?
What motivates them personally and how are they rewarded?
What is their general operating model, aka leadership persona? (More on leadership personas in the following section)
A quick guide to leadership personas
Each boss has their unique style, strengths, and areas for improvement. By understanding these different leader personas, you can tailor your approach to communicate better, collaborate, and achieve your goals.
Here are some typical boss personas you might encounter, along with tips on effectively tailoring your messages to each type.
Of course, I have to mention that no list or categorization is perfect. Many bosses may fall into more than one persona, or there may be personas that aren’t covered here. Use this list as an orientation and a starting point to better understand your boss's behavior and preferences. By being adaptable and observant, you can refine your approach to suit the unique nuances of your boss's personality.
All-Knowing
Description: The all-knowing boss believes they have the expertise and knowledge in all areas. They might come across as overconfident and may not easily accept feedback or suggestions from others.
Tailoring Your Message: Approach them with well-researched data and evidence to back up your points. Present your ideas as enhancements to their existing knowledge. Use phrases like, “I’ve built on your excellent foundation with these additional insights…” to show respect for their expertise.
Indecisive
Description: The indecisive boss struggles to make firm decisions and often delays choices, seeking more information and reassurance.
Tailoring Your Message: Provide clear, concise recommendations and outline the potential outcomes of each option. Make your preferred choice easy to identify by highlighting its benefits and minimizing risks. Use definitive language and offer to take on the responsibility for the decision’s implementation to ease their concerns.
Hands-Off
Description: The hands-off boss gives a lot of autonomy and expects their team to manage without much guidance. They might be difficult to reach for input or feedback.
Tailoring Your Message: Clearly outline what you need from them, specifying the areas where their input is crucial. Provide periodic updates to keep them informed and show you are on top of things. Ask for feedback in specific areas to encourage their engagement without overwhelming them.
Insecure
Description: The insecure boss lacks confidence in their leadership and may be overly defensive or resistant to feedback, fearing it reflects poorly on them.
Tailoring Your Message: Approach them with empathy and positive reinforcement. Highlight their strengths before gently introducing areas for improvement. Use a collaborative tone, suggesting, “I think we can achieve even greater success if we…” to make them feel included and supported.
Risk-Averse
Description: The risk-averse boss prioritizes safety and stability over innovation, often avoiding decisions that could potentially lead to failure.
Tailoring Your Message: Present your ideas with a thorough risk assessment and mitigation strategies. Emphasize the low-risk nature of your proposal and how it aligns with long-term goals. Use examples of successful implementations from other teams or organizations to build their confidence in your suggestion.
Micromanager
Description: The micromanager closely oversees all aspects of their team’s work, often to the point of stifling autonomy and creativity.
Tailoring Your Message: Keep them informed with regular, detailed updates and reports. Reassure them of your reliability by showing meticulous attention to detail in your work. Gradually demonstrate your competence to earn their trust and request more autonomy incrementally.
Visionary
Description: The visionary boss is focused on big ideas and the future direction of the company, sometimes overlooking day-to-day operations.
Tailoring Your Message: Align your suggestions with their long-term vision and goals. Use visionary language and emphasize how your ideas contribute to the bigger picture. Provide practical steps for implementation to show that you can bridge the gap between vision and execution.
Empathetic
Description: The empathetic boss is highly attuned to the feelings and needs of their team, prioritizing well-being and morale.
Tailoring Your Message: Communicate openly about your needs and concerns, as they value transparency and care about your well-being. Frame your suggestions in terms of how they benefit the team and improve morale. Highlight any positive impacts on team dynamics and productivity.
By recognizing and understanding these various boss personas, you can tailor your communication and approach to effectively manage up and build stronger, more productive relationships with your leaders.
Things that are always a good idea for any boss persona
Build trust: Be a helpful resource. Help your boss to know your strengths and what they can rely on you for. This is an important step that makes it much more likely your boss will be willing to accept your feedback.
Be empathetic: Really try to empathize with your boss and understand what they care about or how they’re being evaluated on their work.
Improve your communication skills: Learn how to communicate in a style that works for your boss. Often that means being clear and concise (they don’t have time for you to dive into all the details), making your request clear in the email subject line, presenting different ideas for solutions, and explaining why something is important to them, your customers, your team and you.
Give feedback: People have a lot of assumptions about their bosses—that they’re more senior, more experienced, able to give directions, and are competent leaders. But this is not always the case! Some of them are new to their roles. Even if you want to respect the hierarchical nature of this relationship, you’re still entitled to give feedback.
And make sure it lands well: Before you give feedback, though, it is helpful to understand your boss’s persona (as we covered earlier). Also, consider whether your boss works with an executive assistant. If so, you may need to do some persona assessment on that person as well and then tailor your feedback based on what you’ve learned.
Adapt your solution to the circumstances: There may be times when it makes more sense to take things into your own hands vs. other times when it makes more sense to manage up (explain, influence, clarify your expectations, provide feedback on their leadership style).
And last but not least: Be aware that some situations may need to be escalated together with a peer of yours. This is never fun, but helps you to get unblocked and shows your boss that you know when to ask for help and support.
Final thoughts
I hope this series has equipped you with the tools and confidence to manage up effectively, fostering better conversations with your line manager. By understanding what to expect from your boss and how to communicate your needs, you can enhance your professional growth and team dynamics.
Remember, building a strong relationship with your boss is a two-way street that requires empathy, clarity, and proactive communication. Start implementing these strategies tomorrow and watch as your workplace relationships and career trajectory improve.
Do you have any remaining questions or feedback for me on this series? What piece of advice or which framework was most helpful? I’d love to hear your thoughts as I continue to refine this content! Send me a note at info@petra-wille.de to let me know!