007-How to respond to "stupid" executive asks

It’s a 5-part answer to the question “Why not my way?” that speaks to how executives like to be communicated with a story and paint your plan as the well-thought-out, well-searched, and well-documented strategy it is.

What are executives like? [8:15]

To start, it is important to take a small step back – and maybe a breath, and remind ourselves how executives like to be communicated with, and what frame of mind they are in.

The executive doesn’t know your day-to-day struggle because they are in the ‘big vision’ planning for the company. They are trying to maximize growth efforts on the macro level at every opportunity, stay ahead of the product development curve, limit operations costs as much as possible and balance the demands of their stakeholders.

Often, many executives do things like, acquire a company, decide on an internal efficiency methodology, or make a strategic product development choice (AKA ‘the pivot’) and then favorably imagine how things will go. They may have even formed a plan of what they would like to happen that hasn’t been shared with you.

Executives are typically optimistic, ambitious people, and they have a favorable view of how a particular choice will play out for the company. And because of their position of power, they can expect it will go their way.

When an executive questions a project decision or plan, your job as a project manager is two-fold. First, to demonstrate value in your project execution that aligns with the overall vision your executive is dreaming of. Second, to stay rooted in reality – the Project Management holy trinity of Scope, Cost and Time.

It is your job to bring them the uncomfortable truths that may not align with the macro vision, so it can be dealt with.

The Formula [11:07]

The approach to this is to walk them backward from the end state, outline the constraints, and make it clear what it takes to get there. The reason we need to “walk them backward” is because C level people love a story. They love to be communicated to in stories, they love going along for the ride, and love being part of it.

Executives are moved by story and persuasion, so you need to use that formula to communicate with them.

This formula works for either audience type, you just simply need to change your delivery by their preferred way of thinking. Here’s the formula:

1. State the end goal or driver
2. Describe the known constraints
3. Reveal the discovery of new information
4. Outline the possible paths forward based on new information

1. It is important that during this step, you specifically include the executive ‘plan’.

5. Lead the executive to your conclusion

1. Reiterate how their solution is part of the big vision overall.

Typically, we don’t get to speak directly to executives, so the medium through which this message is sent may change. It could be an email, PowerPoint deck, you could be briefing a senior manager or vice president to talk to the executive on your behalf. Or you could be the lucky person to have to explain this. In terms of format, you need to make sure you have the answers or descriptions to each one of these bullet points, regardless of medium.

Part 1 – State the end goal or driver. [14:28]

You, as the PM and CEO of your project, should have a very clear understanding of what the end goal or driver is from the executive. If you are unsure about what this is – you may be in trouble!

This was covered so well in our 5 part series ‘What are the first 5 questions you should ask when you begin your project’, and you can pull this answer directly from Episode 1.

Your end goal or driver just needs to be clear and concise. Some examples could be:

End Goal

• Integrate the data centers so we have one single location in Singapore for all Compute
• Deliver a new feature before an immovable date

Main Driver

• Reduce processing time for our highest priority transactions by 30%
• Complete an upgrade as soon as possible

If you are unsure at all of what these bullet points should be for your project, do go back and listen to our first five episodes as they will help you answer them!

The most important thing here is that you are reiterating back to your executive sponsor what they have already told you – The end vision for the project you are working on. Make sure you start on even ground.

Part 2 – Describe the known constraints. [17:30]

This is the stuff that the executives either don’t think of, don’t have time to care about, or more likely, they hire you to manage.

Constraints are the pain in the neck part of project management. It is your job to communicate with them and/or overcome them. No one wants to hear about them as they are typically ‘boring’ risk stuff. Or often, people don’t understand that they can’t just be solved with ‘more people’ or ‘more money’. So first, we clearly state what we are up against. To go from our examples above:

End Goal

• Integrate the data centers so we have one single location in Singapore for all computers.

Constraint

• Have 30 min or less downtime for our major services during the transition.

End Goal

• Deliver a new feature before an immovable date.

Constraint

• The budget is set – no additional funds can be requested, use what you have to get it done.

Main Driver

• Reduce processing time for our highest priority transactions by 30%.

Constraint

• If directed a development team and not infrastructure: No matter how much we improve the code, we are limited by hardware.

When it comes to these constraints, sometimes we need to help protect our management team from themselves. Executives are living in the future, where we’ve already achieved our goals. We live in the now, and we want to make sure they move toward our same solution from the same starting place.

Part 3 – What did we discover? [19:42]

Walk through your executive to the same intelligent and careful planning process you went through.

Each project starts out with some amount of unknown. That’s why we budget for contingency, complete a discovery process, and assume that something will go wrong. Your executive does not know the things that led you to your final decision. The purpose of this question is to illuminate what you’ve discovered.

• You may have learned there is ancient code that no one understands or has documented that runs a critical part of transaction processing that needs to be delicately handled in order to speed up processing.

• You may have discovered that the data centers have twice the hardware and services you originally estimated.

It is important to note that you also could have discovered new constraints. Maybe another project team is working on an upgrade with dependencies on your project, or maybe you have a regulatory or customer legal requirement you need to abide by.

Whatever it is that you discovered, you need to share this in ‘executive-friendly’ speak. Again, this will change from exec to exec, but it’s important they understand the gravity of what you have found.

Metaphors and numbers work best in describing constraints. Metaphors can help a less technical audience understand the situation while numbers can help when you’re trying to explain that the scope has increased by a certain magnitude.

It is important that you, as the storyteller, are using this discovery as your ‘plot driver’ for your decision.

Part 4 – What are our options now? [28:14]

Now we’ve gotten to the crux of the problem and we need to determine how we are going to deal with it. It is important that during this step, you specifically include the executive ‘plan’ as they imagined it.

You need to set your executive up to look down a few different paths of solutions. The first one should be what they wanted to do. It sounds a lot like this:

Knowing that we wanted to achieve [end goal] within [constraints], we looked [executive’s idea]. [Executive’s Idea] gives us [positive thing about solution]. However, with [new discovery], it makes us [exceed constraint].

So that’s a hard mouthful to spit out, but in practice, it would sound like:

“Knowing that we wanted to achieve a decrease of 30% in transaction processing time, without changing the hardware, we looked at changing the risk evaluation process and simplifying parts of it. However, with new compliance requirements, we are required to keep each step of the risk evaluation process, and each step is operating as efficiently as possible at this time.”

One way to look at the job of an executive is to make decisions. And that can be tough because if you make the wrong decision, it can be disastrous for a lot of people. The best way we can help when it comes to a request or a problem that needs to be solved is this – we need to identify the options, clearly define them, and make sure the executive understands the benefits and drawbacks of the options so they can make the best business decision.

Part 5 – Lead the Executive to Your Decision [34:57]

Now we’re getting to leading your audience to your ultimate conclusion. We’ve shown the executive what would happen if we went with their preferred solution, so then, what are the rest of our options?

Outline the rest of the options that both 1) your team considered and 2) you feel comfortable presenting to leadership at that level. In practice, this is just a few quick bullet points and can look like this:

Under our proposed plan, we reduced transaction processing time by 28%, maintain

our regulatory required risk evaluation process, and do not require new hardware.

Reiterate Project Commitment to the Vision

Now that you’ve both reminded the executive you reviewed their plan and you have restated your projects intended plan, it is time to remind them how the project is still aligning to their overall vision.

Takeaways

Key Probing Questions

• If you possibly can, ask around why your executive sponsor isn’t supporting your plan, or wants to change it up.
• Does your sponsor have a goal he hasn’t shared with you?
• Is there a new directive that hasn’t been communicated which is driving this request?
• Did you miss something?

You may be in trouble if:

• You never asked those first five questions! Go back and give our first 5 episodes a listen. It’s key to have those questions answered in order to be able to speak to what your sponsor wants to hear.
• You didn’t evaluate what the sponsor wanted in the first place. If so, you shouldn’t be at all surprised they are coming back to you now with these asks.
• You have a new sponsor that wasn’t briefed on the original project goals. The great news is, you can use this formula for a new sponsor!

Principles for Success

• Be confident. Your team is smart and capable, and your solution is the right solution.
• Respect the question. On more than one occasion, we’ve had a stupid ask which turned out to be not quite so stupid as we thought it was.

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