Second in a 3-part series

Reflecting on Business Self-Improvement

It’s a common question people are asking themselves in January: What’s the self-work I need to do this year to make myself healthier, happier, more financially secure.... But as a CEO obliged to your board, employees, and stakeholders, are you asking the same questions of your business?

Imagine pulling together your leadership team this week and throwing out this one agenda item: What self-work do we need to do? You may get some funny looks if language, introspection, and self-reflection aren’t often the explicit focus of your business meetings. But shouldn’t they be?

Navigating Challenges in a Mid-Stage Startup

The other day, I was speaking with someone whose mid-stage startup was coming off a tough year. They’d grown, but they’d missed their plan by a good bit. This was partly driven by economic factors impacting their market, and they have doubled down on that message as they communicate the impact on increases and bonuses.

But that’s not the full story. As an outsider looking in, I noticed they lack effective sales and marketing leadership and integration, let alone coordination or even much in the way of interaction between the two groups. Sales representatives (who also handle ongoing client success), feeling taxed enough by the demands of growing and maintaining the existing customer base, stalled for several months on introducing a new offering to clients. This dramatically reduced its revenue potential. Meanwhile, the marketing team isn’t built to optimize demand generation and lacks an overall strategy. Even worse, there is barely a relationship between the sales and marketing leaders. Despite the results, the company is not taking any specific action on these fronts. But why?

Overcoming Overwhelm and Paralysis

Often, I find that inaction is a symptom of feeling overwhelmed. There is a lot to unpack among these individual and interrelated marketing and sales issues; it’s hard to know where to start, especially when it’s not feasible to invest in everything at once. Sometimes, that causes a company to pick a starting point based on someone’s gut feeling or on what they determine to be “low-hanging fruit,” see what happens and go from there. That’s the launch pad for what we call “random acts of sales and marketing.” The results promise to be as random and scattered as the actions.

At other times, it causes paralysis. It seems like there’s so much to do that we don’t know where to begin. We are constantly driving to figure that out and never moving forward.

True -- it’s not possible to do everything at once. But the answer to that dilemma is neither indiscriminate trial-and-error nor stubborn inaction. Instead, it’s to figure out what really needs to be prioritized so the problem shifts from overwhelming to addressable.

Diagnostic Tools for Business Improvement: Chief Outsiders' Approach

One of the key reasons I’m with Chief Outsiders is that my clients gain the greater benefit of our collective experience. We use three diagnostic tools to leverage the combined insight of our 120 Chief Marketing Officers and Chief Sales Officers to help our clients understand what’s working, where they have challenges, what to prioritize, and how to take the first steps. Each takes only about 10 minutes to complete.

1. The Growth Gears Assessment. This focuses on the fundamental elements of marketing insights, strategy, and execution, as well as overall marketing performance. The comprehensive report shows what is working and where you have challenges while providing tools and resources so you know where and how to get started. Link here to take the assessment.
2. The Sales Readiness Assessment. This analyzes your team's sales readiness across four key dimensions—People, Process, Platform, and Performance—to pinpoint areas of strength and opportunities for improvement. Link to it here: Outgrow (chiefoutsiders.com)
3. The AI Readiness Assessment. We’ll soon invite companies to take this in beta mode. I have the privilege of serving on the Chief Outsiders AI Tiger Team, so I’ve seen first-hand how impressive this tool will be. Get in touch with me if you’d like to be one of our early users.

Realizing Positive Change

I recently met with a CEO to go over the results of his Growth Gears Assessment. We were able to narrow down his marketing focus for 2024 to three top priorities and clear steps to move them forward.

The Sales Readiness Assessment helped a client who has been focusing on developing a marketing strategy and building up its search engine optimization and outbound marketing engine to uncover the first thing to tackle to bolster sales. Now, they are well-positioned to leverage the increased leads. For another company, it helped the two principals to pinpoint where they differed in their understanding of the sales organization; this led to clarity about how to structure a turnaround plan.

My colleague Ed Valdez and I have worked with a fractional Chief Technology Officer firm to leverage our combined AI readiness assessments and develop workshops we use to help companies rationally, strategically, and realistically engage AI for competitive advantage.

Each of our assessments takes about 10 minutes to complete, followed by a 30- to 60-minute conversation to dig in on what the results mean for moving forward.

When we call them assessments, it sounds much more like a business discussion. But, really, isn’t it about doing the self-work your company needs? It’s January. Time for some introspection so you can achieve the growth you need in 2024.

If you’d like to talk about these questions, please reach out to me at dbaker@chiefoutsiders.com.