Project Practitioners > Conversation Starters for PMs and Sponsors - Part 2: Planning

Conversation Starters for PMs and Sponsors - Part 2: Planning

By Sinikka Waugh

What do you say to your Sponsor during Planning?

No single communication relationship in a project is more critical than that between the PM and the Sponsor, but not every PM and Sponsor know how to connect. Every project is, by very definition, unique. But there are predictable moments, and critical conversations that need to take place throughout the project. Assembled below are some conversation starters - prompts, if you will - to help PMs and Sponsors have more effective exchanges duringn Planning.

Read them, make them your own.

If you are a PM - use them to engage your Sponsor.
If you are a Sponsor - use them to engage with your PM.

If you'd care to get ideas on what to say during Initiation, click here:   


CONVERSATION STARTER 8 - (At the very beginning of Planning) Are you ready? 

Congratulations, Sponsor! Initiation is complete and we've been approved for Planning. Congratulations for gaining organizational support for taking a closer look at this idea!

Have you been through Planning before, Sponsor? It's so easy to underestimate the effort that goes into Planning, but this really is a herculean effort! And it’s messy business. We'll try it a couple of different ways, we'll realize we've missed something and have to turn around and redo some things, we'll work on some assumptions that turn out to be untrue, and it will take a couple of go-rounds to get it right. Will you be patient with the mess? We'll deliver a better result in the end if we really get our hands dirty during Planning.

Are you ready for this next step?


CONVERSATION STARTER 9 – How do you feel about Planning?

What kind of planner are you, Sponsor? To be honest, I'm not sure how much you care for Planning, but I'm hoping you're not at one of the two ends of the spectrum. I've worked with Risk-Taking-High-Action-Get-It-Done Sponsors who said "Let's get this planning thing over fast, and jump right in to getting things done" and I've worked with other Cautious-Meticulous-Risk-Averse-Plan-Loving Sponsors who said, "Let’s plan until it's perfect". Neither of those two extremes works really well - we need a balance, something in the middle. Planning is important, and we need to do it well, but we can't delude ourselves into thinking we can actually predict the future.


CONVERSATION STARTER 10 – Can we talk a little about our roles in Planning?

During planning, my primary job as PM is to help us all assemble the pieces. You see, our project is bound by scope (what are we doing), time (how long will it take) and cost (how much will we invest in it), and I get to make sure we create a balance among the three.

Estimating? Me? No, I don't do the estimating for any work that I'm not going to be doing myself. Estimating is best done by those who will do the work - then we bring all the pieces together like a big puzzle to create a viable plan.

Your job, Sponsor? Thank you so much for asking! By the time we leave planning, Sponsor, we'll have a good picture of what it's going to take, but there's lots of work that happens between now and then. Please don't rush us, and please don't let anyone else rush us or prevent us from doing our due diligence. You want a good plan, right? We want to create the best and most realistic plan possible, so we can execute on it.

Planning is where I spend the bulk of my effort as a project manager, and it's no simple task.

So what really is your job? I'm so glad you asked! Your job is to help us plan. Your message during planning is essentially "let's spend a more time, money, and effort to analyze the options, and create a viable plan for delivery - and then we'll review it one more time to make sure it still makes the best sense for our organization."


CONVERSATION STARTER 11 – How long will Planning take?

You mean, “Will we be planning forever?” I can see why you would ask that, and sometimes it has felt that way in the past. No, I'm a firm believer that change will happen, and that we can't predict everything, so we can't possibly plan for everything. If we tried to plan for everything, we'd never get anything done! So we'll plan just enough - enough so we're prepared, and enough so we're all on the same page, but no so long that we lose momentum.


CONVERSATION STARTER 12 – What’s our baseline?

In order for us to achieve those benefits we described in initiation, Sponsor, we need a baseline understanding of where we are today. For example, are we expecting to reduce talk-time, increase through-put, eliminate costs, or increase revenues?

We won’t be able to prove that we’ve improved unless we know where we’re starting from. Can you help us get that baseline, Sponsor? Does someone in the organization already have that information? Can you connect us? Do we need to measure it for the first time? Can you help open some doors so that measurement can be taken? 

As you well know, no one outside the project team has spent as much time with this idea as we have, so they might need a quick summary of what we're doing and why. Here's a section from our charter document, Sponsor, that might be useful to share with those we’re involving now…


CONVERSATION STARTER 13 –Where does this project fall in the line of organizational priorities?

As businesses today, Sponsor, you likely know we only have the resources to do about 60% of what we want. What that means to us is one of two things:

First – it means that something else isn't going to get done, in favor of this project.

Do you already have an idea of what will be a lower priority for you (or for the source of funding) than this project, Sponsor? What will have to wait, or be put on hold or cancelled or stopped in order to work on this?

Incidentally, now's probably a good time to ask, there anyone who feels passionately about that thing that's going to get put on hold? You see, a stakeholder is anyone who is impacted by this project - and, well, put yourself in their would you feel about another project that came in as a higher priority than yours and took away all your resources? We'll have to find some way to help them feel okay about this.

Second – the resource limitations means that we, too will get bumped by higher priority efforts.

Do you already have an idea of what will be a higher priority for you (or for the source of funding) than this project, Sponosr? How far down the list are we? That’s an area of risk we need to keep our eye on as we go.


CONVERSATION STARTER 14 – How much are we talking about here?

So let's talk about money a little, Sponsor. I'm sure you've already given this some thought, and no one really likes to talk about money, but the sooner you and I talk about it, the sooner it won't be hard to do.

Sponsor, do you already have a dollar or a range of dollars in mind? How much? Where's the budget for this project going to come from, do you think? Are there other funding sources we can go to, if it winds up being more expensive than we think?


CONVERSATION STARTER 15 – When do you need this thing wrapped up?

Let's talk about time a little more, Sponsor. Another topic I'm sure you've thought about. What were you picturing in your head already? Now please don't misunderstand, I'm not saying that we'll meet that time line you're hoping for, Sponsor, - how could we possibly know since we’re still figuring out the work that needs to be done? But it's important for me to understand what you were picturing.

Is there a business reason that the project work needs to be complete by a certain date, certain month, certain season, Sponsor? Are there operational calendars, customer peak-seasons, industry considerations, or weather that impact this project's success? I mean, if we were in the business of making lawn mowers, then we would need to set our time line around the design, manufacturing, marketing, distribution, and sales training steps that need to happen before lawn mower buying-season, right? What time constraints do we need to think about here?


CONVERSATION STARTER 16 – How is our communication working for you?

My goal as PM, as we talked about in Initiation, is to help drive this project home for you, Sponsor, and to connect with you the way that works best for you. How is our communication working so far? What can I do differently to be more effective for you, Sponsor?

What communication points do you have with your peers and leadership, and how can I help you feel prepared for those, Sponsor?

The team really will need to see you engaged and active during Planning, and we’ll likely have questions for you along the way. May we count on you, Sponsor, to attend our regular team meetings, at least every other meeting, for some portion of the discussion? How can we make that happen?


CONVERSATION STARTER 17 – Can you help us get the resources we need?

Once we figure out what it's going to take to complete the project, I'm going to need your help getting the resources, Sponsor. I can't just walk over to Joe's desk and ask him to start working on this project. Can you help me talk to Joe's leader and secure the amount of Joe's time we need for this effort to succeed?


CONVERSATION STARTER 18 – How good is good enough for you?

From a project management standpoint, I’m committed to the right level of quality for every aspect of the project – not just how good the end product is, but also how close we stay to budget, how well we met our schedule, how well the team functions together, how effective our communications are, how happy and engaged our stakeholders are, and more! But how good is good enough is up to you.

Are you a perfectionist, Sponsor? Perfection takes time and money, so I want us to be deliberate about meeting your needs. What’s most important to you? Perfection is a direction not a destination, really, so we won’t have 100% perfect scores on everything, but what’s your comfort level for going over or under budget, going over or under schedule, going over or under scope, etc.?

And from a stakeholder perspective, when we keep them happy "enough," who are your priorities? It’s really hard to keep everyone happy, but I’ll manage more closely to those you help me prioritize.


CONVERSATION STARTER 19 – How are you with surprises?

Yeah, I know, most of us don’t care much for surprises. I get that, Sponsor, but you’ve asked me to manage this project for you, and I don’t want to pester you with every little thing. I know you’re busy, and I want to strike the right balance for you.

Personally, I like to use the phrase “raising a yellow flag” to mean that we’ve identified an issue in the project that has the potential to take us off track. It hasn’t done so yet, and we’re actively managing it, but we may still need your help if our plan doesn’t work. Will that work for you, Sponsor?


CONVERSATION STARTER 20 – What risks do you perceive?

Sometimes I ask, “What could possibly go wrong?” but that question may not work for you. So tell me a little more about you, Sponsor, and how you think about risks.

    • Are you an optimist and a gregarious story teller, Sponsor? Then I won't ask you what you're afraid of, I'll ask you to tell me a story about another project you've seen that you don't want to have happen to us. 
    • Are you an analyst at heart, Sponsor? Then I will show you the tools I use to help us analyze and prioritize our risks. 
    • Are you a directive risk-taker who values brevity and self-directed action, Sponsor? Then I'll state our risks in an actionable way that already demonstrates to you what we're doing about them. 
    • Are you a process-person who prefers to have consistent and logical processes, Sponsor? Then I'll show you the risk management process, and give you time to absorb what we're doing and consider your response.


CONVERSATION STARTER 21 – (At the end of planning) What’s most important for you?

Before we leave Planning, Sponsor, I need you to put these three items in priority order – number them 1, 2, and 3. Scope (delivering what we said we would), Time (delivering when we say), Cost (coming in on budget). Which of those is highest priority for you?

You see, they form what we call the iron triangle or the triple constraint. What that really means is that in Planning, we'll create a balanced triangle to help us succeed, but that along the way we know something will change. That’s pretty much the only thing we can guarantee! We’ll learn something that we don’t know today or think of something new, and that information will cause us to change the project’s scope, time, or cost.

We can't change any one side without adjusting the others (for example, if we add scope, then we must also add time or cost), if we remove time, then we must also remove scope or add cost). I'll protect the side you value most, and that will be the one that changes the least, but we'll have to be able to make adjustments as we go to the others.

So which is most important to you, Sponsor?

I can see that doesn’t resonate with you, let me try another approach to see if I can help.

My brother used to work in an IT services shop, and there was a sign on the wall that said, “Do you want it quick, cheap, or good? Pick two”. The idea here is that we can’t have all three – if we want it good, it will take more time or more money.

    •  What if we really don't deliver all of the scope you've asked for? Then what? Can we still be successful if we only deliver some of it?
    • What if we can't meet the stated time line, and we go over by a day? A week? A month? Then what? How will that impact our success?
    • What if we can't meet the stated budget, and we spend an extra $1 $100, $100,000? Will we still achieve our goals?


Okay, in that frame of reference,Which one side (scope, time, or cost) is most important to you, Sponsor? Which one can't change, but must stay firm.  What’s second? Do you understand that means that the third priority is the most flexible, and we may have to sacrifice it to protect the others?

As PM, I’ll protect the one that’s most important to you, Sponsor, and I need you to know that we’ll need to flex that third side from time to time to accommodate the changes that come our way.


Thanks, Sponsor, I know that was a lot of questions, but planning involves a lot of our heavy lifting, and all the work we do now will pay off in the long run.  Thanks for making time for me, and for investing in our working relationship!  I appreciate you, and I'm glad to be working wiht you on this!


In the next installment of this series, our PM and Sponsor will move into Execution for more scripts.  Stay tuned for the next step!


 Readers:  Do you have other ideas for kickstarting those critical PM/Sponsor conversations during Planning? Chime in the conversation and add your comments below.


Sinikka Waugh, President and CEO of Your Clear Next Step, LLC teaches and coaches individuals and teams on how to interact better with others and get things done well.  Learn more at


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