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10 Big Questions to Ask when Kicking-off Important Marketing Initiatives

by Frank Cowell | Updated Nov 9, 2021

There’s a Lot on the Line for CMOs and VPs of Marketing These Days

Today, more than ever, CMOs and VPs of Marketing are being given “quotas” in certain aspects of their overall marketing performance. While this is not a totally new conversation, the advent of content and inbound marketing (and it’s measurable nature) has brought the spotlight back on this conversation. Because of this, it’s more critical than ever to ensure that marketing initiatives are well thought-out before jumping into execution.

Over the years, I’ve found that the biggest factor in marketing success has to do with how an initiative is started. By this, I’m referring to the nature and quality of “kick-off” that you as the marketing leader are responsible for executing. During this kick-off period, it’s imperative that you set expectations, get aligned, and create positive team energy. This can make or break your initiative’s success — it’s that important.

The Kick-off Meeting is Critical to the Success of Your Initiative

One of the very early events during this period is the “kick-off meeting.” This meeting is the formal commencement of the initiative, of course. Typically, these meetings are about getting down to brass tacks, which is necessary. What’s often missing, however, is connecting all team members to the “why” as well as getting everyone to think “big picture.” Connecting the “why” and getting everyone to think “big picture” will ensure that you create ownership, excitement, and fresh ideas — all critical to your success.

Through this experience, I’ve developed a list of 10 “big questions” that can be bolted-on to the beginning of any kick-off meeting. These questions, really, have nothing to do with a “project.” Instead, they have everything to do with creating the team alignment that is critical for success. If your initiative includes people from outside of your close-knit team (other divisions, outside vendors/agencies), this exercise is especially important.

These are the actual questions that I use in kick-off meetings all the time at my agency. I like to think of my kick-off meetings as an “exploration.” I hope these questions will help you explore your team’s potential during your next big initiative!

10 Big Questions Every CMO and VP of Marketing Should Ask when Kicking-off Important Marketing Initiatives

1. Why are we here?

Upon first seeing this question on the screen, people sometimes are taken aback. “What do you mean, ‘why are we here?’?!” is the look on their face. I love this question, it really sets the tone. It’s a heavy question that, maybe, nobody has bothered to ask throughout the process.

As part of this question, you want to expand the commentary by following-up with, “What is the compelling reason to invest significant time and money? Why not leave things the way they are? What would happen if we did that?”. By directing the conversation down this path, you can get to the truth. It ensures that the group commences the initiative from a place of honesty, cutting through the bullshit.

As a result of this conversation, you’ll uncover the core imperative. You’ll uncover the “why?” of the initiative. Your first step in creating alignment, excitement, and positive team energy.

2. What are our overarching business goals and objectives?

Your initiative might be to “plan and execute our content marketing program,” which will, naturally, have its own goals and objectives. Now is now the time to talk about those goals and objectives, however. First, you want to talk about the organization at large because you want to make sure that everyone on your team has a clear picture as to where the organization wants go.

Objectives such as “The organization wants 25% of the hospitality market share by 2018,” might seem very distant to the initiative at hand and one might wonder why the entire team should spend any time discussing it all. The reason you do this, however, is because these goals and objectives are going to sit in the subconscious of the team while they strategize your current initiative. And while sitting in their subconscious minds, this information will be like kindling, igniting new ideas about how to go about solving the current problems at hand.

Additionally, you’re also building the “why?” story, which, as I stated above, is critical in creating alignment.

3. What makes us so special?

Another cut-through-the-bullshit question that I love to ask. This forces everyone to eliminate the marketing fluff and get down to the (very few) things that make your organization worth engaging. If you were to audit your “reasons why” list, you’ll probably find that most of them are just “table stakes.”

In reality, there are very few things that make your organization that much different than the next. Your goal here is to acknowledge that and hyper focus in on them. In doing this, your team will only infuse the absolute best attributes of the organization into your initiative.

In case you aren’t catching the theme, with this exploration, you’re creating a place of total transparency and honesty with your team — a magical place where amazing things can happen.

4. Where are we falling down?

This is kind of the antithesis to the previous question — you’re looking to be honest about what’s not working and what you totally suck at in your organization. By exploring this area, you’ll ensure that your team doesn’t try to go down a path of “owning” something that’s not realistic. That being said, if this initiative is specifically meant to turn around an area you are falling down in, then just be mindful of the true position of the matter.

One way to explore this is to list the top three challenges your organization is facing or will soon face. By putting a ranking on your organizational challenges, and limiting to only three, it forces the team to focus on only the biggest challenges. After all, you’re not looking to create a gripe session, nor are you wanting to beat everyone down with a depressing conversation.

Another option for this part of the exploration is to ask “What are we afraid of?”. This question is especially good when the organization has been going through rough periods as it allows the team to express concerns, release anxiety, etc.

5. Which of our competitors should be on our radar?

While I’m not a fan of obsessing over one’s competition, it is a good idea to get a quick pulse on what key competitors are doing to ensure that you are zigging when they are zagging. During this portion of the exploration, only focus in on the extremes — what they are great at, what they suck at, recent moves they’ve made, and what they are rumored to do in the near future.

Again, you’re not looking to spend a ton of time here, just get a refresher on what those other jerks are doing.

6. Where have we had branding and marketing challenges?

This is your bridge from the big picture conversation you’ve been having to the initiative at hand. During this part of the exploration, you want to understand which marketing initiatives have gone off the rails and why. This is another area in which you are going to help create an atmosphere of transparency and honesty.

If you’ve had a good exploration to this point, you will have established trust among your team. This is important because you’ll want the team to be willing to be vulnerable and feel like they are in a safe environment — an environment free from finger-pointing.

7. Where have we had branding and marketing success?

Now that you’ve had some cleansing, it’s time to acknowledge and celebrate the successes your team has had. When discussing the various “wins,” ask “why?”. It’s not enough to know which initiatives were successful — you want to uncover the gems that made them successful.

You’ll often find that successful initiatives can be tied to one or two critical components. I often find that the critical component is when more time is spent in strategy and planning vs. execution. But, that’s my experience. Yours may be completely different!

8. What might possibly limit or impact our strategy, direction, or execution?

Does your CEO often want to poke his or her head into the initiative, change things up, causing complete chaos? Do you have a finance team that has tons of red tape before outside vendors can be paid and initiated? Are funds limited? Is there a drop-dead date? Are there skill sets needed that your team doesn’t have?

These are just a handful of examples of the types of things that could have serious implications on your strategy, direction, or execution. Plan for your CEO to poke his or her head into the initiative. Get dates and commitments from them on the calendar at the outset. Talk to your vendors about the on-boarding process before a contract is signed. Ask them to start gathering needed paperwork so it’s ready when finance starts asking for it. Identify the skill sets your team lacks. Budget and look for outside help from Day 1.

You get the point.

Addressing these issues now will ensure that you don’t create a plan that ignores your realities, causing inefficiencies, missed deadlines, and overall heartache.

9. Are there key milestones or events coming up that we should be aware of?

OK. This is your last chance to get some of the key logistical information out on the table before you dive into the specifics of the initiative. Knowing about and planning for key milestones and/or events will ensure that you plan around these moments.

For example, the Q1 Board Meeting will be held a couple of weeks before your first presentation is due, and you are pretty sure they are hoping to see it at the meeting. If compressing the timeline to get the presentation done before the meeting isn’t possible, then what kind of “presentation” can you prepare and have ready at that point? How about having that conversation with the executive team the moment you know about these dates instead of hoping that you can work everyone to death to make an unrealistic deadline?

10. Who is our customer?

By “customer,” you’re not looking to get the definition of your company’s customer — that should shake out as part of the specific initiative during a target audience analysis. Instead, the “customer” I’m referring to is your internal customer. That is, “Who are we serving within our organization? Who do we need to make happy? What does success look like for them?”

If you’ve read any of my other posts, you’ll know that I believe “marketing” is a services organization and, as such, service means that your are providing a service unto others. Who is your other and what is important to them?

Marketing, like everything in life, becomes much sweeter when it’s about serving others, rather than our own interests.

Don't Forget, The Better Your Strategy, The Better The Final Product

I cannot stress enough how important the Strategy is to your initiative. By having a good Strategy and Planning phase to your initiative, you’ll ensure that you have the smoothest Execution phase possible. Trust me — it’s a hell-of-a-lot easier (and much more cost effective!) to do the “back-and-forth thing” during Strategy and Planning than during Execution.

To make sure your next marketing initiative is built on a strong initial strategy, be sure to fill out your Digital Utopia Blueprint, which will be your guiding light throughout the rest of the journey.