How to Make Smart Professional Asks

How being intentional when asking for professional favors and advice leads to more successful outcomes.

Author

Devin Keane
January 24, 2024

Read time: 4 minutes

Hi Proactive Professional,

It turns out, most people suck at asking for things. They typically just blurt out whatever they need without taking a second to think about if they

  • Can accomplish it on their own

  • Are asking the right person 

  • Are giving the right context 

I have a terrible habit of asking for where something is right as I begin to look for it. It could be a piece of clothing, scissors, or any object in our apartment. But if I spent just 20 seconds looking, I could probably find it on my own.

Inevitably, it goes something like this:

Devin 5 seconds into looking: "Mel…do you know where the remote is"

Melissa: "Did you even bother loo-”

Devin 20 seconds into looking: "Never mind, found it!" And I go about my day.

Luckily, I try to be much more self-aware when making asks in a professional setting. (Don't worry, Melissa, I'll work on the personal side). I try to take an intentional approach, which separates a thoughtful ask from a transactional one.

“After all, if you go around asking everyone you know for help, or if you make the wrong ask at the wrong time, it can seem transactional.”

In fact, Superconnector has a great framework that I've adapted for making an ask. Let's explore more below.

How to Make a Good Ask:

1. Pre-Ask Checklist

âś” Is the person I'm going to ask the right person to make the intro I'm seeking?

Willingness to help does not mean they are the right person to do so. Think about if the person you want an intro to would be excited to hear from them or confused (or worse, annoyed). Would be received the right way by the end party?

âś” Does someone who does not understand anything about my industry or business understand my ask?

Are you being clear enough so they know to make the right introduction and are able to communicate the ask with appropriate context?

âś” Can I figure this challenge out myself or through an available means so I don't waste social capital?

Have you looked into if you can accomplish what you are asking on your own? If not, do your due diligence.

2. Avoid the Lazy Ask

You need to be specific about what you need and why you need it. Otherwise you are just creating frustration and work for the person you are making an ask of.

Avoid the following:

  • Giving zero info beyond “does anyone know someone at company X?”

  • Giving poorly thought out or half-baked asks

  • Offering lots of info about yourself but no info about why it’s a mutually beneficial connection and how it makes sense

  • Giving lots of info but none of it is relevant

When you do those things, you don’t show why you should be connected and you don’t prove that you’ll use the connection in a mutually beneficial way. After all, the person you’re asking has a reputation to maintain. Make sure it's worthwhile for them.

3. Making a Good Ask

A good ask should be rich with context, comprehensive but concise, and have a high likelihood of success.

Consider the following:

  1. Be concise: The ask should be simple, straightforward and take 30 seconds to convey. Lead with what you are trying to achieve, not how you want to get there.

  2. Target the right person: Don’t confuse this for the most senior person. It’s the person or type of person that can actually help you.

  3. Make the other person a “thought partner” with you: If you aren’t positive about how to get to your desired end result, bring the other person in to help structure or direct your ask appropriately.

  4. Set realistic and achievable expectations: Don’t give some lofty goal. Instead, start simple and even mention the time commitment on their part to make them more comfortable in saying yes up front.

So, next time you want to blurt out an ask to someone you think can help, pause for a second and understand if you are being intentional. If you haven't considered who you are asking, how you are conveying the message, and why you can't figure it out on your own, you probably aren't.

Otherwise, you'll probably get a similar response to when I ask for the remote…

What I’m committing to this week for building relationships (time commitment ~5 hours):

  • âš˝ Co-hosting Pitch on the Pitch: Soccer Networking for Tech, on Thursday at 7pm ET. Sign up here! (~2 hours)

  • 🌆 Attending a Yorkseeder's tech social (~1.5 hours). If you are in tech, check out the Yorkseeder investor, founder and tech hub here

  • 🥂 Reconnecting with the first person I worked for as an intern over drinks (~1 hour)

  • 🤔 Reflecting on my week this Friday: What can I do to reduce impulsive asks in my professional and personal life (~15 minutes)

What are you committing to this week? Reply to this and let me know!

Best of luck building,

Devin