How to Make a Good “Ask:” Context, Clarity, and Communication

Let’s first talk about what this piece is not about: It is not about deciding what to delegate, to whom to delegate, or what you do versus what you ask others to do. Let’s assume you’ve worked through these decisions and now the one thing you are missing is how to make a good “ask” on an important project or assignment.

Let’s talk about how to have a good “ask” conversation. Note, first and foremost, this is a two-way conversation. But before you can have a conversation, you need to know what exactly you are asking.

Where This All Started

A few weeks ago, I had the opportunity to be involved in a program focused on feedback. It was a great program that appropriately focused on the feedback model: how to start the conversation, how to gain clarity on next steps, giving individuals time to practice, and so forth. 

But, as my mind is apt to do in these situations, it started to wander. Not to the beach, or to the mountains, or to my “to-do” list. Rather, I started to wonder (in my wander) how many of the occasions when feedback needs to be provided in organizations might disappear if the initial “ask” were only clearer.   

In other words, how often do we make “drive-by asks” (e.g., “Hey, can you pull those numbers and get me something by next week?”) that create confusion and unclear expectations?  

I asked the facilitator of the program about this during a break. Neither of us had scientific data come to mind, but we both concluded that a good, healthy, sizable percentage of situations when feedback is needed would indeed go away if leaders focused more on making the initial ask a good one.   

Begin With the End in Mind 

It is always a good idea to begin with the end in mind. Think for a minute about this question:

If someone was going to delegate a significant project to you (or your team), and that person REALLY wanted to set you (or your team) up for success, what would you want to know coming out of the “ask” meeting?

Pause for a moment to really think about all the things you would need to know.

When I think about how I would answer this question, the things I would want to know fit into three broad categories: Context, Clarity, and Communication.

1) Context

With respect to context, your colleagues need to understand the larger problem that you are trying to solve. This is not what you are specifically asking them to do, but rather how the “ask” fits into the bigger picture, why it is important, and how it contributes to the business or other stakeholders.

Individuals need to see the broader context and understand how what you are asking them to do fits into that context. After you make the “ask,” that person should be able to answer these questions:

• What is the broader problem we are trying to solve or the issue being addressed?
• How will this assignment fit into or contribute to the broader solution?
• Why is this an important assignment?
• Who will benefit? (e.g., a customer or another department)
• How will it create value for the organization?

2) Clarity  

On the clarity front, first and foremost you need to get clear in your mind about what you are asking the person to do, and then you need to make it clear to them. This is not a time for being vague or assuming the individual understands what is being implied. The first place to get clarity is on what specifically you are asking them to do. Here are a few categories, ranging from least to most empowered:

• Investigate: bring back organized/structured information.
• Investigate: bring back recommendations with analysis and reasoning.
• Take action: start executing, but consult on key decision points.
• Take action: communicate ongoing progress.
• You decide: reporting results.
• You decide.

You may find that the category needs to change as time goes on. You might choose an “investigate” option at the beginning, and then later transition to “take action” or “you decide” once more information is acquired and the requirements are clearer. It is important to keep in mind that this initial conversation is just the start of an ongoing discussion. 

But that is just the start of achieving clarity. After the “ask” conversation, the other person should be able to answer all the following questions that are relevant to the project:     

• Who might I need to work with to get this done, and what have they been told about the project and my role in it?
• Who are the key stakeholders of the solution? Who will approve, implement, and support the work, or who could impede or cancel the project if they are not bought in?
• What does a successful result look like and how will that be measured? If this is not already established, is it my job to work with the various stakeholders to determine the key criteria and metrics of success?
• Are there any constraints in terms of time, money, other resources, or in the solution itself?
• How does this project, the skills I will learn, the people I will work with, and the network I will build contribute to my current and future success? In other words, what is in it for me?

3) Communication  

Finally, you need to set clear expectations as it relates to communication: most importantly is determining how your colleague should keep you updated on progress. Regardless of what you are asking them to do, individuals should know how, when, and in what format to communicate progress, and when to consult others in the context of key milestones.

At every stage of the project, the individual should know:

• What key milestones or other information needs to be communicated?
• How often should I provide progress updates (with calendar dates established)?
• What format(s) should I use for this communication?
• What will success look like?

Remember: the “ask” is a conversation where both parties co-create agreements on follow-up, milestones, key metrics, and so forth. This should be a conversation, but it should be a conversation where you, the leader, have gained clarity in your mind about what you are asking others to do.

Whether you are asking someone to book travel reservations or to work on larger-scale projects, making a better “ask” can significantly reduce time-consuming confusion and the need for feedback after the fact. It ultimately will set you, the person to whom you are delegating, and the organization up for success.

But, for now, the focus here is just simply to provide…

Context. Clarity. Communication.