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Anonymous Career Advice

Self-Taught Manager Issues?

 This week’s anonymous career advice comes from “middle manager with middle manager problems”. 

Dear focus, I am a self-taught manager and I struggle managing my team and manage my manager’s expectations. What is the best way to develop my management style of managing my manager and managing my team? 

There is something quite important about understanding you can improve as a manager and improve managing those around you and those you come into contact with regularly. 

An issue managers face is typically being able to create time to manage, to do their own work and manage out managers, or at least their expectations. 

Middle management is the hardest area of management, it is often the time you learn most about the work environment, the way people are motivated and what expectations truly are. 

Personally, I have a belief that management is an art form that a tiny per cent of people have managed to crack, it evolves every day and with every interaction, so this advice won’t be perfect but will be a guide to help you improve as a manager and improve communications and expectation management.

Management Advice

Managing up 

Managing up is about relationships and time management, most senior managers are time-sensitive and struggle to have much time to dedicate themselves to one to ones or one to few. 

From experience key to managing up is to communicate the most important aspects and goings-on with clear thought and in digestible chunks. Being able to have an exec summary and a list of objectives and the ways you are thinking of tackling those objectives often puts you on the front foot. 

One issue to countermeasure is handling the requests and helping your manager to know when you can take more work on and when they need to take work off you. This happens with a relationship and having clear one to ones and clear communications around hurdles. 

One problem two solutions framework will help greatly with overbearing bosses as will risks vs benefits framework when going through and managing your communications. 

Managing Around 

Managing around you is an area many ignore as managing those managers in the same position as you are is an important part of your development and building a support network. 

Managing Your Team 

Managing your team is always a challenge, something that has been a help in my career is working out the individual motivations and the way people want to be managed and compare to how you manage them. Surprisingly you will find some are motivated by praise, others are motivated by money and some are motivated by knowing they can improve. 

Being able to have open conversations, help problem-solve together and collaboratively and speak on the right level will help you have better relationships and improve as a manager, being trusted and proving you have their best interests is vitally important. This comes with time and having their back and supporting them by knowing when they need you, when they want you and when they don’t know they require support and guidance. 

An important lesson: saying my door is always open and not being available is something that upsets and frustrates your team far more than you will know. 

More actions you can take to proactively progress as a manager:

  • Hire a professional coach 
  • Ask for internal mentors 
  • Look for external mentors – costs can vary but important to know how much an external mentor will improve and challenge you differently
  • Hire a personal development coach 
  • Join a manager group – some can be particularly useful, be wary of HiPPO bias or admin bias in big groups
  • Build a management group on slack, discord or on LinkedIn to improve your skills and be able to have voice anonymous issues. I have built a number of communities that have helped greatly  
  • Write a professional and personal SWOT – this will help you spot your own weaknesses and build on opportunities you and others see
  • Read lessons from leaders this was an important set of interviews from last summer
  • Bringing those up around you will improve you as a manager, consider is it time for a co-pilot
  • Ask to co-create leadership principles to roll out to your leadership teams if this does not exist and will enable you to understand different situations and working environments particularly if you have access to broader teams, for instance: tech vs non-tech management are completely different challenges.

Leadership is not a linear journey and often you learn more in challenges than you do when everything seems to be going well. 

Keep up on knowing you want to progress and being proactive in developing out your career. 

Finally, never discount free resources on YouTube, LinkedIn and don’t be afraid to invest in books. 

Have Your Own Question?

Our book recommendations can be found 

Focus book recommendations 

5 Business Books To Read 

Ride of a lifetime  – The Disney Chairman autobiography

The Netflix Company Culture Book aka No Rules Rules – – The Netflix CEO book autobiography


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