TL;DR: Asking why is a key strategy in your content marketing efforts. Building a culture where your team has time and feels comfortable stopping to ask why takes planning and practice. Don’t let strained project timelines and egos keep you from utilizing this important tool.

Over the past week, I’ve run into situations with two very different clients around their overall content strategy. In both cases, their marketing teams are executing at a high level, but have missed something in their feverish drive to create content: asking WHY. And this covers a lot of “whys” that should be asked—for example:

• Why this channel?
• Why this content?
• Why this cadence?
• Why this audience?
• Why are we making this assumption? (Is it an assumption? Do we have data to back this up?)

And then we can start to even dig in to process questions:

• Why this SME?
• Why this tool?
• Why do we do this like this?

Of course, then I can’t help but ask my own why—why aren’t these teams taking the time to ask why? This is a two-pronged cultural issue. Part 1) They don’t feel empowered enough to ask why and 2) the organization isn’t building in a place to examine their strategy often enough. Let’s look at these.

Why They Don’t Feel Empowered

This has happened to me so many times, it will likely feel familiar to many of you: there was one time, maybe a handful, where you DID ask why. You questioned a tactic or a piece of the process and got shut down. You heard something like “That’s just how we do it here” or “That’s not your place to ask why this came from higher up” or in the agency world “That’s what the client wants”.

I’m telling you now that if you want to produce the best work, these questions need to be encouraged and actively SOUGHT OUT.

No Time

Why are these questions being snuffed out? One is obvious: deadlines. Sometimes we’re moving so fast we think we don’t have time to stop the train and ask why the cars are in that order. But what if the order really matters? What if it’s critical to the safety of the train? Okay, in marketing we don’t have lives at stake, but slowing down and asking why can save us a lot of hassle and even bigger delays down the road.

How to fix it: Process

Pride

The other more insidious reason these questions get run over is ego, which is often disguised as a time issue. Look, I get it, no one likes to have their methods or plans questioned (especially by our kids), but we’re doing ourselves, our team, and our results a huge disservice when we let our pride override the opportunity to improve. We need to make space for these questions to be asked AND answered.

How to fix it: Process

Making Time & Space for Why

I’m sure the process bullets I’d give you for solving the time issue are obvious and not super helpful, but I’ll give you a few anyway. Where I think most orgs need the work and process is creating a way for teams to feel safe and comfortable asking why.

Building Time for Why into Your Processes

At the Project/Campaign Level

Let’s start with the low-hanging fruit: building out timelines and milestones in a way that gives our team time to be thoughtful. But in reality, timelines never work quite the way they’re supposed to, even when we have the best intentions. The key is to build reflection into those timelines—create a literal subtask that is a look-back.

Does this piece that we’re working on still fill the need? Has something significant changed in the world that makes this campaign sub-optimal? We have grown used to doing this around events like queens dying and natural disasters, but this is a reaction. What we want here is action: what if something else happened with the company or a competitor that means we need to make a pivot? In this case, we frequently fall victim to the sunk cost fallacy: we’ve already put so many resources toward this campaign/tactic/event that we HAVE to see it through. (One could argue that this case also falls under the PRIDE umbrella.)

So when do we take this step? Where does this fit? Who’s responsible? Great questions that I would love to answer. But your existing team and process have to be considered. Ultimately, whoever is responsible for the overall campaign should be asking these questions on a regular basis. This person should have an understanding of the campaign as it fits into the overall strategy and a close understanding of the purpose (and if you’re in an agency, a deep understanding of the client). It could be added to their check-ins on the project. I’d recommend it come way before the final sign-off. It’s even harder to stop or change something that is basically done.

At the Strategic/Planning Level

Man do I love a beautifully scheduled year-long content plan. Each quarter has a focus and each month a theme. It’s just so satisfying. But it’s also SUPER dangerous because we do it, wrap it up in November for the next year, head out of the holidays and come back in January ready to execute and never think about the plan ever again.

WAIT. What? Yeah, yeah. Remember the last time we did that and everything fell apart? I’ll give you a hint, it was 2019 and then 2020 ate all our content plans for breakfast, lunch, and dinner.

I’d like to say we learned our lesson, but I don’t think we have. In fact, in the case of the clients I mentioned, they haven’t really examined their overall strategy in years. They just keep going like Wall-e without addressing the larger context of *everything*.

You have to build review into this process, too. At the very least on a quarterly level. It doesn’t mean you have to scrap your plan and start over everything 3 months. But you might have to. The key here is to be brave enough to ask the questions at all and then have the guts to do something about it.

I think that’s what’s really at the heart here: fear of finding out we were wrong or that something isn’t working. What’s worse? Finding out something your team is hard at work on probably won’t work due to whatever external reason or continuing blindly and finding out at the end? Well now we’re into feelings and pride and shame and so it’s time to talk about the next reason folks aren’t asking why.

Creating the Space for Why

This is definitely the trickiest to implement because it’s about the culture of your organization more than anything. Once you’ve built in places for review of tactics and strategy, now you have to hope your team feels safe enough to actually ask the questions. But Jensie, you told me earlier that process is the solution to this issue, just tell me how to do it.

In this case, the process you need to put into place is coaching your team to respond positively when people are asking why. Active training and modeling of curiosity and openness, rather than defensiveness and ego. So maybe this is a little bit of process and a lot of practice. For process, you can start with the interview stage in being open and praising curiosity. And keep it up—build a safe space where new folks never hear “that’s just how we do it here” or “that’s how we’ve always done it”. Sure, there’s a time and place for that feedback. With my new hires, I ask them to keep a list that we can look at after they finish onboarding. I WANT to hear their thoughts, but I want them to have enough context before we dig in.

I get it, it is SO hard not just to snap respond and put our egos aside. But this is where practice comes in. Practice have hard conversations. Practice waiting a beat before reacting. And for pete’s sake, separate your value from your work! Feedback on a process or plan or deliverable isn’t personal. If you work hard to build a culture that is focused on the success of the org, everyone should be working to that end—rarely if ever is someone out to get you or make you look dumb.

Need more help here? I highly recommend Daring to Lead by Brené Brown. She really digs into shame/ego/vulnerability and how that impacts us as leaders.

Some Final Thoughts

I can look back on some very specific times that I didn’t ask why and absolutely regret it. I got sucked into the sunk cost fallacy (we’ve spent so much time on this email series, we have to use it) more than once on campaigns, hiring, and other big and small things. Personally I’m working on asking why a lot more, both at work and at home and having the guts to say it out loud and make changes. It’s really not an easy thing to do, so start small and trust yourself—that’s the first step. You won’t be able to change your whole team or org overnight, but you have to start somewhere.