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The Bloom Room: Your boss says ‘be more strategic’. Now what?

Jess Wood and Kristy Emmanouil explain how to turn vague feedback into clear calls, sharper insights and stronger plans.

By The Bloom RoomPublished Nov 12, 2026
3 min read
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Still sitting on that question because everyone else in the meeting seems to know the answer? We’ve kept you a seat.

The Bloom Room is back for week two, with bloom strategy’s Jess Wood and Kristy Emmanouil tackling the questions that keep media and advertising people second-guessing themselves - from winning business to managing teams and getting a good idea beyond the brainstorm.

Drawing on careers across publishers, platforms, agencies and the creator economy, they’re back with practical advice for Mediaweek readers. No need to disguise your question as “more of a comment”.

Pull up a chair.

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Question: It’s planning season, and my boss says I need to be more strategic. What does that mean, and where do I start? 

Answer: “Be more strategic.” Great. But what does that actually mean?

If it helps, your boss may not be entirely sure either. “Be more strategic” is one of the most common bits of feedback in our industry and one of the least explained. It comes up in reviews, in 1:1s, and in passing hallway chats.

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Strategy is about choices. What do we focus on, what do we leave out, and why? When a leader asks you to be more strategic, they want to see you make those calls yourself instead of putting everything on the table and hoping something sticks.

Look up before you look in

Most of us open the planning doc and go straight to what we’re selling. New formats, the rate card, last year’s spend plus ten per cent. This year, start with your client instead. What’s changing in their category? What’s shifting with their customers? What will their CMO be judged on next year? That’s where the good ideas are.

Know your data from your insight

Data tells you what happened. An insight tells you why it matters and what your client should do about it. A plan full of data looks busy. A plan built on one sharp insight shows your client something they hadn’t seen in their own business.

Have a point of view

This is the big one. Strategic thinking shows up when you’re willing to say, “Here’s what I think we should do, and here’s why.” One clear recommendation you can defend is worth more than five options with no opinion attached, because a list of options leaves your client to do the hard work, while a recommendation tells them you’ve already rolled up your sleeves and done it for them.

Build the bridge

The best plans connect the client’s problem to your solution in a line anyone in the room can follow. This is where most proposals fall over. We get excited about the idea and forget to show how it solves the problem. Always start with the client’s problem, in their words. Then show how each part of your plan helps fix it.

Where to start this week

Pick your three biggest clients. For each one, write a single page answering these questions: What’s changing for them next year? What problem can we help solve? What do we think they should do?

Keep it rough. Then take it to your boss and ask for feedback on your thinking, not the slides. You’ll quickly find out what “strategic” means to them.

Strategic thinking isn’t something you either have, or you don’t. It’s a habit, and it gets built by asking better questions earlier and backing yourself to answer them. Planning season is the best time to start.

If you want a question answered by The Bloom Room, email: [email protected] 

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