Great Managers Don’t Hold Umbrellas

It’s time to let your team get their feet wet

Emily Sheen
Management Matters
6 min readFeb 6, 2024


Image Credit: Writer’s Own

One of the most popular management mantras has been to “be the umbrella” for your team or “be the human shield”. A great manager should protect the team from distractions so they can focus on their tasks without sweating stakeholder stress.

Makes sense, right? But what happens to managers who are effective umbrellas? And what would happen if their employees got their feet wet? Is an “umbrella boss” best for the team in the short and the long term?

What does it mean to be the umbrella?

Cedric Chin at *Management for Startups* sums up the role of a manager as “increasing the output of the team” and explains that one way to do this is to act as an umbrella or shield, “protecting the output of the team from the natural randomness that occurs in any functioning organisation.”

By “natural randomness” he means senior stakeholders expressing competing priorities or new information that will distract the team’s focus.

In his words, “this isn’t anything controversial”, but are there tradeoffs involved with being the umbrella in the long-term?

Well, it depends on the weather.

Light Rain

It’s drizzling, but your umbrella is up anyway. There’s not much for you to protect the team from right now and although they’re not getting wet, they’re also wondering what you’re doing — deadlines are tight and they could really use some help on the ground.

As a manager in umbrella mode, you might be so focused on the sky: “it looks like rain”, that you forget to roll up your sleeves when your team most needs support.

If the team is coping fine, but feels disconnected from your updates to others in meetings they’re not part of, they might feel demotivated.

Strong communication is a must to make sure everyone is on the same page and no one feels completely removed from the wider business implications of their work.

Forbes writer Rebecca Fraser-Thill explains that in order for work to feel meaningful, everyone on the team needs to be able to:

  • Understand who benefits from their work (even if the impact is far away from their contribution)
  • Interact with the people who benefit
  • Feel part of a collective
  • Believe their contribution is “unique and significant”
  • Find and define their own sense of meaning in their work

In shielding the team from even light challenges, a manager can sometimes stop individuals from seeing the full picture and understanding the impact of their contribution, which is demotivating.


It’s pouring, and the rain is coming at you sideways. Drenched, you resolutely hold up your umbrella but the team is getting wet regardless. And because you held the umbrella when the rain was light, they have no context as to where this downpour has come from.

Confused and uncomfortable, they wish they’d had some warning and felt more prepared.

Even the most effective umbrella-wielding managers will not be able to entirely shield their team from a downpour. Once the team starts to feel the effects, they will experience a context deficit and start to feel misled. What’s driving these changes? Why aren’t things going well?

At worst, the team believes the manager hasn’t been transparent and that their brave face was insincere.

In his book The Hard Thing About Hard Things, Ben Horowitz describes a similar error of judgement in his journey as a young CEO: “I thought I should project a positive, sunny demeanor and rally the unburdened troops to victory. I was completely wrong.”

Whilst putting on a happy face and repeating “everything is fine” feels like the noble thing to do, complete denial of challenging circumstances dissolves trust and leaves team members feeling disconnected to the realities the organisation is experiencing.

Chin explains it’s a delicate balance between two extremes: “how much withholding [of information] is too much? Where is the line drawn?” and suggests a good rule of thumb is to err on the side of transparency wherever you can, except where it might affect motivation.

This is all well and good until the downpour becomes a storm. How to keep everyone motivated whilst being transparent?


The wind is up, and the umbrella has turned inside out — the storm is too much to weather alone and you leave your team exposed to the elements as a result.

For teams whose managers have shielded them from the worst of the downpours, this comes as a shock. The manager has been plugging gaps in the leaky ship so seamlessly that it’s felt like a smooth journey for those on board. In fine weather, this might have been dubbed “great leadership”. But as the weather picks up, this approach inevitably leads to overwhelm. The manager can no longer plug all the holes in the leaky ship and water starts pouring in without warning.

At worst, the manager’s mental health crumbles and the team collapses, because they’re ill-prepared for this sudden exposure to the elements. At best, reinforcements are brought in at the last minute and it’s an uncomfortable and bumpy road to recovery.

What’s the alternative?

If it’s ok to be the umbrella in a light shower, but an ineffective strategy once a storm is brewing, what’s the alternative?

Once the storm has set in, it’s too late to do anything different. The team are experiencing a context deficit, with little understanding of how things had begun to head south.

They want to step up to support, but have been denied the opportunity for so long, it’s difficult for them to do so. In his Harvard Business Review article on the topic, Luis Velasquez explains that umbrella management leads the team to adopt a “disempowered stance” that doesn’t prepare them well for a crisis.

The best that can be done at this late stage is to communicate clearly: what happened? What can we change? What’s next?

Instead, imagine a world where the team got their feet wet when the rain was light. They’ve had exposure, got a handle on the context and are ready to step up when the storm sets in.

As the storm hits, the team rallies and faces it together, each plugging holes in the ship with full trust in the manager to share progress and setbacks so they can react accordingly.

How? Because up to this critical point, the manager didn’t hold the umbrella. They filtered out the noise without totally shielding the team, freeing up their own emotional bandwidth to give more support.

What does this look like?

For those of us still clinging on to the umbrella, here are 3 ways to ditch it and create a better experience for our teams.

Share Context in Real Time

As a manager you often have the benefit of foresight, seeing roadblocks ahead. This means you can share regular updates on:

  • What you’re navigating with the team: “right now there are a few roadblocks with legal — I’ll keep you posted”
  • Who is seeing their work: “yesterday these were the areas the clients were particularly wowed by and these were the areas where they had questions”
  • The impact it’s having: “the extra time we took to create a clearer, simpler narrative really landed well”.

Let it Go

Holding tight to your umbrella often looks like refusing to relinquish tasks, especially those that feel ‘risky’ to delegate. This strategy only breeds greater reliance on you and fails to prepare others to step up or take over.

Finding a way to let go bit-by-bit and offering feedback to course-correct along the way gives teams the opportunity to step up and leaves everyone more energised.

Give Questions, Not Answers

Another way many of us protect teams is by coming up with solutions for them. This only reinforces bad habits as it doesn’t encourage anyone to think independently.

Instead, ask questions and see what solutions others come up with — you may find they’re stronger alternatives to your own perspectives.

“We’ve hit a bump in the road. What would each of you do to solve this?”

It’s time to ditch the umbrella and hand out the ponchos. Preparing your team for the storm may turn out to be the best thing you can do for their career and your own.



Emily Sheen
Management Matters

Incurably curious human with contagious 'big room' energy. Happiest helping people grow. Singapore-based 🇸🇬 startup builder, team leader, coach and DJ 🎵