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Getting things done Part 3: Prepare Yourself

Updated: Jul 2




Let’s say you have a great idea for a solution to a problem that’s been plaguing your team and you can’t imagine why anyone wouldn’t immediately say yes. Except when you explain your idea to your team lead the conversation goes wrong and your idea goes no where.

Presenting a new idea, pushing back on a bad one, asking for something, delivering bad news, raising risks are all common conversations that can go wrong.


Getting Things Done Series


Create a plan for important or hard conversations 

Through trial and a lot of error I’ve learned that a little preparation helps things go more smoothly. My friend Cip and I always used a whiteboard to plan. I’ve created a series of worksheets for my team so they can self-serve if I’m not around.


Don’t forget the setup 

I’m impatient, I always want to dive right into discussion. My friend Cip is the master of the setup, he makes sure that the person(s) he’s speaking with know the background, objectives and what we want to accomplish in the conversation. Clients, stakeholders and especially executives are very busy people, quickly remind them of what we’re doing and where we are in the process so they can make a decision.


From there you can describe what’s happening and why it is a problem or opportunity. For example, “We are trying to do these stories, but we’re blocked because an api isn’t ready. We’re at risk not having the feature for the March release when the sales team needs it for the conference”


Make an ask 

If you want someone to do something (give permission, take an action, invest money) you need to ask them to do it. I’ve seen many people present ideas and but not ask for action. Don’t assume that your audience can read your mind.


They’ll likely need to know the cost or impact before saying yes, let them know how much or long it will take,  possible impacts and how we move forward


Be prepared to answer questions and objectives 

Consider the perspective of the person or people you are talking to and list all of the questions, concerns or motivations they have. Then start thinking of ways to answer so you are prepared if it comes up. If you discover a big risk, then be upfront with it.


Practice or role play (yes really)

It can be incredibly awkward to practice or role play a conversation. But going through things with a friend will help you think through things, refine your point of view and give you more confidence. You may worry that you will become too rehearsed or robotic, I seriously doubt that will happen.


Image: This series uses photos from Central Parking at Logan Airport. It's my favorite garage art installation.

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