How to Overcome Sales Enablement Challenges | Part 2: Engaging and Involving Sales Managers

After having discussed the “lack” element of sales enablement challenges last week, this week we are going to talk about challenges around sales managers such as sales manager misalignment. Yes, sales managers seem to be involved in various sales enablement challenges in many different ways. Let’s take a look at what you told us.

In the open text responses from our 4th Annual Sales Enablement Study, you shared some sales manager-related challenges that can be summarized in three buckets: a) misalignment with sales managers, b) missing sales manager development and c) a lack of driving adoption and reinforcement of the initial sales enablement initiatives for salespeople. Misalignment typically is the most important issue to be resolved first as, for instance, the adoption and misalignment challenges are just a consequence of enablement and sales managers not being on the same page.

Key challenge: Sales enablement is often disconnected from sales managers. (click to tweet)

This is a situation I encounter more often than not. Amazing sales enablement strategies have been developed, mapped out and even funded. In theory, they usually make a lot of sense and address the root causes of the challenges to be solved. However, there is an enormous gap in many shiny enablement strategies: lack of implementation.

Any lack of implementation strength and focus is a serious danger for sales enablement and for you as a sales enablement leader. (click to tweet)

Implementation success in sales is only possible with your sales managers. It won’t work without them, and it certainly won’t work against them. And that ultimately brings us to the role of sales managers, especially frontline sales managers.

Sales managers are the linchpins in every sales organization who have to drive the implementation of any sales strategy. (click to tweet)

That requires sales managers to lead their teams in a way that they can achieve their goals and focus on the implementation of new strategies at the same time. Frontline sales managers are especially where the rubber meets the road: in the field. They are the only role that directly leads six or more quota-carrying salespeople.

Who is the most important influence for any sales professional? It’s their direct sales manager. It’s not sales enablement, it’s not sales operations, and it’s usually not their sales leader. It’s their direct manager, because that’s the person who heavily impacts how they sell, where they sell, what they sell and to whom, and how they are supported… or not.

Imagine that the sales managers are not on the same page regarding your sales enablement strategies. Imagine they have a different focus, or they take an entirely different approach — or they don’t coach at all. What will happen? No implementation will ever be successful. And transformation won’t happen at all.

Not having sales managers involved and engaged in your sales enablement strategy puts your investments at risk. (click to tweet)

Yes, it’s that drastic, even if you have senior executive buy-in. Let me be very clear with that. Even if you have senior executive buy-in, which is a prerequisite in itself, you have to engage and involve your sales managers directly and personally. If you don’t take the time to involve and engage your sales managers early on, you will have a very hard time landing any sales enablement success.

Let’s discuss a few steps to help you engage and involve your sales managers, even if you currently don’t provide and services for them.

  • Build relationships first, and make them personal.
    If you are new to the organization or the sales enablement role, your sales managers are an abundant source of street wisdom. Whatever challenges exist, they know about them. Building mutually beneficial relationships is the first step. Asking for their perspective, as you want to make sure that you correctly address the selling challenges, is a starting point. In most organizations, sales managers are not often asked for their perspective, as they are often the role blamed first if the numbers aren’t what they are supposed to be. As they have heard of your plans via their bosses, it’s important to build relationships first and set your approach into their context.
  • Ask them for feedback on your plans early on, and listen to their challenges.
    Before you pitch your ideas and strategies to them, listen to their daily challenges, thoughts and concerns. They will have great perspective on how any implementation will work (or not) in their teams and across the organization. Integrate their feedback into your implementation plans. Ask them what they expect and what they would prioritize now.Let’s say that a manager has issues with meeting goals as the team approaches a new industry, and most sellers struggle with confident, valuable and relevant conversations in that industry and new buyer roles. Take that as an opportunity, and create a pilot for that team.
  • Build a group of highly engaged sales managers as your early adopters.
    Even if you are in an organization that didn’t implement sales coaching development for sales managers yet, you can collaborate with them to achieve your shared sales goals. In my previous role, I gained a ton of street wisdom from working with a few excellent sales managers who were very positive regarding sales enablement and simply wanted to use everything that could make them more successful. Ask for feedback if you implement something new (e.g., a playbook). Integrate their feedback, and let them test it with their teams. Then make it perfect, and roll it out.
  • Let sales managers promote your enablement services.
    If that happens, you have taken all the right steps. As they are the key role for sellers, that’s the best scenario you could ever ask for. If sellers hear from their managers that resources and tools have to be used or certain behaviors are expected, it’s 10 times more powerful than sales enablement communicating it alone. And in an ideal world, these sales managers also coach their teams along those lines.
  • Ask them what they need to become even better coaches in their role.
    That opens the space to discuss a sales manager enablement program with sales coaching at its core. You can only have this conversation with them if you earned their trust beforehand and can prove that your stuff really works.


Stay tuned! Next week we will discuss the biggest successes you shared with us!


On another note, because research also needs study participants, we just launched the survey of our 5th Annual Sales Enablement Study. We’d appreciate you taking 15 minutes to participate in this survey so that we can continue to help you! Click here to get started!

What’s in it for you? You will be among the first to receive the full report, before it is open market; you can download a members-only research asset right after completing the survey; and you also are invited to become a member of our research community.

Thank YOU!


Questions for you:

  • How do you involve and engage your sales managers?
  • If you are already involving and engaging your sales managers, how did you get there?
  • If you are not already involving and engaging your sales managers, what stands in your way right now?

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