Ask The Pointed Question – The Best Retention Strategy Is Leaving No Stone Unturned
By Alicia Marr – Transformation Director at Hogarth Australia

Ask The Pointed Question – The Best Retention Strategy Is Leaving No Stone Unturned

By Alicia Marr – Transformation Director at Hogarth Australia  

Imagine a world where we invite people to say exactly what they mean. We hold space for them to tell us – we listen – and we action.  

I’m a big fan of asking pointed questions. Although I must admit it has been out of necessity rather than strategy. As an Autistic person, I have always struggled with the nuance of human emotions. I know they’re there; I can see a shift in how someone feels, but I often don’t know exactly what to do with that info or how best to support them. One day I stopped trying to read people’s minds and I just started asking them. They knew how they were feeling – so I should probably just ask the experts. My toolkit was filled with:  

  • What isn’t sitting right with you about this?  

  • Talk me through what you’re feeling right now  

  • If I was to hypothesize that we do X, would you say that’s on track or do you think that’s off the mark?  

  • How can I best support you in this moment?  

A recent TikTok by Heather Elkington sparked a new era of asking the pointed questions with this gem “If you were to hand your notice in tomorrow, what would be the reason?” 

I almost crushed my thumb adding it to favourites and then I wondered if we could do the same for our clients. In my career I've seen firsthand the challenges agencies face when it comes to retaining valuable clients. In today's competitive market and pressure on CMOs to do more with less, it's critical we stay connected to client needs, concerns, and aspirations. 

A simple yet powerful strategy: Just ask them where they're at. Regularly. And then do something about it.  

The Power of One Pointed Question 

At least once a quarter, make it a priority to ask this pointed question to your most senior client/key decision maker:  

“If you dropped our agency tomorrow, what would be the top reason?” 

Yes, it’s direct. It might startle them a little at first, and you’ll need to make sure you leave space for them to answer. That means, under no circumstances should you speak before they do. Ideally, you’ll open a dialogue to uncover hidden issues, unmet needs, or brewing dissatisfaction and end up with invaluable insights into the health of your relationships and areas for improvement. 

What if they say everything is fine?  

That’s the beauty of the wording of the question, you’re not asking if they have any feedback or how they think things are going. You’re simply asking for the harsh reality. Cold hard facts. Answers may range from things like cost, inefficiencies in ways of working, lack of proactive ideation etc. Whatever it is, at least you’ll know what to tackle for the next quarter.  

On the off chance they do answer with ‘everything is fine’, then you still have work to do – because ‘fine’ shouldn’t be the standard and I’d argue that it’s also not a strong indicator of a good relationship anyway. Imagine if your best friend was getting married and they described their relationship as ‘everything is fine’. You’d tell them to high tail it out of there and expect more from a long-term relationship.  

The Pointed Question vs Agency Feedback Scores  

Agency feedback scores and the Pointed Question both offer valuable insights and serve different purposes. You’ll always need both. While feedback scores are valuable, they don't always capture the full picture. The Pointed Question approach complements these scores by uncovering hidden truths that may not be reflected in general satisfaction ratings.  

The Cost of Sticking Our Head in The Sand  

The costs of losing a client in agency land, whether it’s creative, production, or media –is it a big hit on the bottom line, but often means redundancies, restructures and saying goodbye to beloved team members. And although I couldn’t find any official reports on how much time agencies put into RFPs and pitches – as the person who writes a fair few of them, I can confirm it consumes quite a few lives for the time until pitch. Not to mention the lead time of the relationship building which can start 24 months out from when we’re asked to pitch.  

Let’s just say the customer acquisition costs are high.  

We also must consider that there’s more competition than ever when it comes to creative, production and media with self-serve options, creator marketplaces, AI tools and more. We must deliver on scale, creativity, technology, but most of all – service.  

Make it Happen 

With CMOs in their ‘do more with less’ era, retention has become mission critical – and it’s time to start asking questions. If asking the Pointed Question still feels a bit uncomfortable to you or your team, remember that feedback is a gift and an opportunity for growth. It is a way to prove your commitment to client success, rather than as a threat or criticism of your work. 

Schedule those check-ins. Ask those tough questions. And most importantly, be prepared to listen and act on what you hear. Your clients, your team, and your bottom line will thank you for it. 


Alicia Marr is Hogarth Australia’s Transformation Director. Working across strategy and transformation for client growth. Designing efficient and effective Creative Op Models for the future, supercharged by AI and production innovation.  

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