How to Know When It’s Time to Bring in External Training

By Kristen Hayer

As an executive, I leaned away from external training.

That may sound ironic given that I founded a firm that provides external training to other companies. But my bias was simple: if we could build it in-house, tailor it to our environment, and save the budget, we should.

In many cases, that instinct was right. External training should not be the default solution every time something feels off. It also should not be the last resort after performance has already eroded.

It should be a deliberate choice. The real question is not, “Should we bring someone in?” The real question is, “Are we the right people to deliver what our team needs right now?”

Here is a checklist to help you decide:

1. Do We Actually Have the Bandwidth to Do This Well?

Building quality training takes time. When we build a one-hour class, we allocate roughly 16 hours to outline it, design the materials, create worksheets, and write the talk track. If you plan to film or record it, double the time for production and editing.

Early and growth-stage companies are often moving too quickly to invest that level of attention. Leaders try to squeeze training into evenings or between meetings. The result is rushed, underdeveloped sessions that check a box but do not build capability.

If you do not have the time to build it thoughtfully, you likely do not have the time to build it at all. Rushed internal training is often more expensive than external training because it consumes attention without improving performance.

Ask yourself:

• Do we have the focus and time to design this properly?

• Or are we about to deliver something half finished?

2. Do We Have the Skill In-House at an Instructor Level?

Leadership does not equal mastery of every skill your team needs. You may be a strong operator but not a skilled facilitator. You may understand renewals deeply but not know how to teach renewal strategy in a way that sticks. You may have instincts about value conversations but lack the structure to break them down for others.

Look internally first. Can another team help? Is there someone in your organization who can teach this topic at an instructor level, not just perform it? If not, that is not a failure: It’s clarity.

If you cannot confidently teach the skill at depth and scale, bringing in someone who can may be the responsible move.

Ask yourself:

• Do we have true expertise?

• Or are we stretching beyond our depth?

3. Are Our Messages No Longer Breaking Through?

I remember being a VP and feeling frustrated because I had told my team the same thing for six months. Then an external trainer came in, delivered the exact same message, and suddenly behavior changed.

At first, it was annoying. Then I realized something important: My team heard from me constantly about dozens of priorities. My voice had become familiar. Even valid guidance blended into background noise.

An outside perspective can cut through that noise. It can lend credibility and urgency to a message that leadership has already been reinforcing. If your team needs to hear it from someone else before they act on it, that is not a leadership failure. 

Ask yourself:

• Have we been repeating guidance without seeing behavior change?

• Would an outside perspective create a reset?

4. Do Credentials Matter in Our Context?

In some industries and regions, credentials are not symbolic, they are structural. Certifications can influence promotion paths, compensation, and perceived credibility. They can matter for hiring and retention. In certain markets, formal education is tied directly to career mobility.

Refusing to invest in credentialed training in those environments can quietly limit your team’s advancement. Part of your responsibility as a good leader is to support not only the present, but the future career path of your team members.

Ask yourself:

• Do certifications influence level or pay in our organization?

• Would formal credentials help our team move forward?

5. Would Broader Education Elevate Performance?

I went back to school when I was a Director-level Sales and Marketing leader because I felt stuck. I believed that an MBA might open doors. It did. But not for the reason I expected.

The degree itself did not change my trajectory. What changed was my perspective. I learned how to think more broadly about business. I learned to speak like a CEO. I elevated my ability to engage at an executive level.

Sometimes your team does not need more tactical instruction. They need a wider lens. External programs, higher education, or executive-level training can elevate strategic thinking in ways internal sessions often cannot.

Ask yourself:

• Is our team operating tactically when they need to operate strategically?

• Would outside exposure raise the bar?

When Not to Bring in External Training

External training is not a cure for structural problems. Do not bring in outside training if:

• Leadership is not aligned.

• Managers are unwilling to reinforce new behaviors.

• You are hoping training will compensate for unclear strategy or broken systems.

Training cannot fix a lack of clarity at the top.

In Conclusion

External training is not about outsourcing responsibility. It is about making a deliberate investment when the return justifies it. Used well, it strengthens your system. Used reactively, it becomes another expense.

The difference lies in how thoughtfully you decide.

The Success League is a global customer success training and consulting firm. If you’re looking to elevate your methodologies and models in your CS program, our Structuring Your CS Program series would be right for you. Additionally, The Customer Success Talent Playbook is a great guide for learning how to hire, grow, and thrive in CS.

Kristen Hayer - Kristen is the Founder & CEO of The Success League, a global, customer-focused consulting and training firm. Kristen’s background includes leading award-winning sales, marketing, and customer success teams in early and growth-stage tech companies. She is the host of several podcasts on CS and leadership, and has written over 100 articles on the field of customer success. The book she recently co-authored with 5 other CS thought leaders - The Customer Success Talent Playbook - recently hit #1 on Amazon in 5 categories. Kristen received her MBA from the University of Washington and splits her time between San Francisco and San Felipe, Mexico.