16 Questions to Ask Your Clients to Avoid Misunderstandings, Resentment, and Excess Work

Being able to work from a laptop with international clients is very sexy… that is, until you recognize the plethora of roadblocks that can occur from not being in the same physical space.

In my time working with clients and team members in a digital capacity, I’ve learned a lot about how to cultivate strong communication through asking clear questions. And these questions were often hard-won.

They are the result of tasks done not once, not twice, but often three or four times over again.

They are gifts given from resentment and passive aggressive behavior.

They are the fruit of learning my own boundaries.

And I want to give them to you because I believe that strong communication builds strong relationships.

Because isn’t that what we’re all here for anyway?

In short, these questions will help you beyond just being a stellar team member. They will help you feel more satisfied with your work, more supported, and more connected in a virtual space that often draws us away -- instead of toward -- others.

Ooh! Pretty thing! - 6 Questions for discussing new ideas, tweaks, and shiny objects

Being an entrepreneur myself helps me exercise compassion when one of my clients has a new, big idea that she really wants to move forward on… but doesn’t necessarily have the energetic space for it. Or the new, cool platform that promises to increase revenue by 67%. Or wants to make a kajillion billion tweaks to her website because she watched an interview with Marie Forleo and Derek Halpern.

I LOVE implementing new ideas and bringing them from paper into the actual world, but I also love when my clients feel focused, know their priorities, and can tick off achievements one after the other.

So while I don’t play “negative Nancy” (or, to be more gender-inclusive, “Norman”) when these topics are brought up, I do like to ask questions with the intention of finding the best solution for both my client and her community.

  1. What’s the motivation behind this project?

  2. Is this a priority?

  3. Do you have the energy (instead of time) for that project? Let's break it down into tasks, and see what it would entail.

  4. What do you already have on your plate?

  5. Since your plate is already so abundant, what can we table for now in order to make space for this new project?

  6. Given that we’re already juggling one too many balls in the air, can this task wait for another two weeks/a month/until next quarter?

Are we done here? - 5 Questions for knowing if you’re finished

I believe strongly in continuing to optimize and iterate, and I also believe, just as strongly, in getting the damn thing done. Because, quite often, if you don’t just put it out there, you won’t know the best ways to improve it. So in order to stop your clients from endlessly trying to iterate in a vacuum, here are five questions to light some fire under all of our asses.

  1. What’s your ideal so-happy-we’re-here outcome for this project?

  2. What specific numbers can we attach to this project to measure our progress against? What would be good? What would be better? And what would be best? (Sending love to my client Adria DeCorte for this one)

  3. What’s our timeline for this project? By what date do we want this to launch/go live/grace the world with its beauty?

  4. Is this ready to move to translation/editing/recording? - Shout out to my client Helen Iwata for this one. :)

  5. Is this ready to go live?

Hey, you okay? - 5 Questions to create a safe space and say goodbye to unnecessary obligation and resentment

Humans create businesses, and we are emotional, so that means emotions often run high and horizontal and vertical and low in business, too. When that happens, it’s better to open a discussion and lay out your concerns. Here are some questions to facilitate those conversations.

  1. You seem unhappy with the way this project turned out. What did you have in mind instead? Where do you think we deviated from that vision?

  2. What’s up? What’s on your mind? I’m here for you.

  3. I’m noticing a lot of resistance around this task. Could there be another reason you haven’t moved forward on it? What do you think is holding you back?

  4. It might just be me, but I’ve been feeling like you’re not 100% satisfied with the progress we’re making. If that’s true, is there anything I could be doing differently?

  5. Are you actually enjoying this task? How open are you to closing the Facebook group/deleting the Twitter account/letting go of it?

What about you? What questions have you found helpful when collaborating online? The more, the merrier. :)

Hi, I’m Cher!

I write about the place where business + social responsibility meet. When I'm not researching whatever my latest obsession is, you can find me re-watching Remember the Titans, posting on Insta @chertakesprettypictures, or hiking somewhere in the PNW. If you're interested in working with me on a marketing or PR campaign, I do that, too.

Click here to find out more.