Middle Management March Madness


Here at Envision, we have front row seats for The Great Reshuffle, and boy oh boy is this game riveting - it’s March Madness indeed! We’re watching Boomers gleefully retire, Gen X taking the helm, and Gen Z leading with their hearts. Meanwhile, Millennials are working hard to bridge the communication divide between them. With all the excitement, it might be easy to miss the smartest play of the game: KEEPING YOUR MIDDLE MANAGERS!

So what’s your game plan to retain your talent in this Great Reshuffle? Here are our strategies to build a winning bracket! (#GoSports!)

  1. Holding your managers accountable isn’t good enough. Your managers are not just responsible for their own deliverables–they’re also responsible for getting their staff to perform. And that can be a pretty tall order in today’s morale-defeating world. So, are you giving your managers the training, coaching, and mentoring they need to succeed?  Yes, communicate accountability, but here’s what more you should be doing: 1) Onboard your managers, 2) Provide ongoing and annual training, 3) Offer peer mentoring, and 4) Check in regularly to support their development, help with conflict resolution, and encourage their self-care!

  2. Recognize their leadership style and help them own it! Steve Jobs is so 2000. Today’s workforce is celebrating and demanding a different kind of leadership: the kind that cares about them and provides certainty, a sense of belonging, and empowerment. When you see something working with the team, tell your manager to dive into it. If you’ve got a manager who brings in homemade cookies and their team goes wild with productivity, send that manager to culinary camp! Put your own cookie-intolerance aside, it’s working!

  3. Model the management values you want to see. How you manage your managers is likely how they are managing their staff. Are you sending emails at 11pm, dropping tasks on staff at 5pm, and telling people to be on time to the office while you’re logging on from your home office in bunny slippers? Or are you giving constructive feedback and public recognition? Do you conduct wellness check-ins, talk to people about their career aspirations, and give them attainable goals? Be the boss you want to see under you.

  4. Are you promoting the right people? Don’t just go by tenure and education level. We’re not going to lie–we like those things–but what makes a good supervisor is so much deeper than that. We suggest you reassess your performance evaluation tools and promotion practices, align performance behaviors with core values, and, once you promote that person, help them succeed! (See #1 and #2!)

  5. What is your communication culture? “Just one more meeting. Please, pretty please!” Is that really what you’re hearing? Haven’t you noticed one of your staff is sipping from a mug that says “This could have been an email”? Your internal communications are a mirror for your culture. Design your calendar carefully i.e. an all-staff meeting, a department meeting, a couple of project meetings, “No Meeting Fridays,” “Wellness Wednesdays.” Make all your meetings 60 minutes and aim to finish in 45, so you can give your staff that 15 to spend however they need. Send out agendas ahead of time, distribute action items afterward, and recap key announcements on Slack. Most importantly, leave time in the week for actual work!

Now hurry up and take action before your MVP winds up “casually looking” on our Current Searches page!


More on ALL OF THIS in the upcoming Equitable Nonprofit Workplace Report.

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