3 Reasons Middle Management is So Hard

We asked 3 managers about the biggest challenges they face.

Just ask Malcolm: the middle is a tough place to be.

We asked 3 middle managers about the biggest challenges they’re facing in 2023.

Meet the Managers

Ben Braun is a Professional Services Director at Esker, a Global SaaS & professional services firm. 

Michelle Wee is the Marketing Director at Britax, the leading safety technology brand (think car seats & accessories).

Our third guest is a Product Manager at a B2B SaaS provider for financial institutions.

The TL:DR?

The 3 biggest challenges our special guests face are:

  1. Moving from Strategy to Execution

  2. Managing Change

  3. Reporting on Progress

Read on to hear from our leaders.

Challenge #1: Moving from Strategy to Execution.

Ben Braun, a Professional Services Director at Esker, a Global SaaS & professional services firm, explains his focus for 2023:

“The theme of this year has been alignment; getting everybody marching in the same direction.” 

In most organisations, senior management is clear on the Strategy. Leaders know the direction they want to go in. 

It’s then up to middle management to deliver this big-picture vision. 

Translating the blue-sky strategy into an actionable plan, constrained by resources, is a major hurdle.

With many businesses now working on a cross-functional project basis, collaboration & alignment among teams is more important than ever.

Challenge #2: Change is the only constant

Michelle Wee, Marketing Director at Britax, told us that helping her teams deal with change is a key challenge:

“With anything, when you introduce new systems, new processes, people have that tendency to be reluctant to get on board. For me, it’s about making sure that transition is smooth.”

Ben Braun agrees, explaining:

The hardest part of my role would be keeping up with change, for sure.” 

Forbes magazine highlights that since the pandemic, leaders must not only tolerate ambiguity, but embrace it.

This can be a daunting situation for middle managers to face every day. 

Challenge #3: Reporting on Progress, ALL THE TIME. 

A Product Manager at a B2B SaaS provider for financial institutions told us she spent up to 10% of her time reporting on progress to various stakeholders across different layers of management.

We need to provide updates to GMs & other senior stakeholders in monthly forums, weekly executive meetings & regular company updates.

There's also multiple other forums that we provide updates to. There's a lot of crossover [in reporting].”

There are extensive, bespoke reporting requirements for different audiences in mid to large organisations.

These detract from managers’ ability to do what matters most: solve problems & lead their people.

Getting ahead: Addressing these challenges

More & more of our customers are looking to technology tools like monday.com to solve these challenges.

Strategic frameworks like OKR are another topical way to build alignment, adapt to change & share progress concisely.

Whether you’re already using OKRs or you still think OKR is an airport in Europe, our virtual OKR Showcase will show you how leading teams build alignment, adapt to change & share progress concisely using OKR.

Join our virtual OKR Showcase

 November 23rd at 11am AEST.

Places are limited so don’t miss it!