Questions to Improve Problem-Solving Skills and Empower a Winning Sales Team

Great sales leaders are problem-solvers.

They have the ability to see around, beneath, and within complex problems to find smart solutions and take the best possible action.

And there is no better way to do that than by asking the right questions.

With the examples in this guide, learn how to improve problem-solving skills by asking questions that clarify issues, create solutions, and empower your reps to convert a sticky situation into a new opportunity.

What does good problem-solving look like?

We thought we’d ask the experts: What exactly does good problem-solving look like?

According to the Apollo team, here are the qualities of a stellar problem-solver:

“In my experience, a good problem-solver is someone who takes any challenges or hurdles thrown at them and is somehow able to find the solution even if it means looking under a rock for it.” – Gerardo Benitez, SDR

“A good problem solver is someone who’s incredibly curious. Having an authentic curiosity in understanding the problem allows you to uncover all components of the problem, including the root-cause, vs rushing into an early conclusion without all of the necessary data.” – Erik Arellano, Sales Manager

Great problem-solvers are strategic and open-minded. They are receptive listeners who prioritize collaboration, communication, and creativity. When it comes to managing a sales team, there are infinite opportunities to exercise these qualities. Common problems that arise in sales organizations include:

• Poor email deliverability and open rates
• Unsatisfied customers creating negative buzz online
• Internal disagreements around sales processes
• Poor objection handling with prospects
• Overly long sales cycles
• Unaligned marketing and sales departments

Sales is no walk in the park; and one of the most important sales manager skills that will help you eliminate these roadblocks is asking both yourself and your team the right questions.

Find the right solutions with these problem-solving questions

Questions for clarifying the issue

• What happened?
• How big is the problem?
• What have you tried?
• What do you mean by XYZ?
• What are the stakes? Who are the stakeholders?

You can’t solve problems if you don’t understand them. Before jumping into developing solutions, always start by asking questions to uncover the whole picture.

Clarifying questions also helps you prioritize tasks and resources. Sometimes a problem isn’t as important as it initially appears (or other times it’s more so). Sales managers who understand exactly what’s happening and where the stakes lie can properly use their time and resources towards finding an appropriate solution.

Questions for creating solutions

• What are ideas for next steps?
• What do you think would happen if you tried X? What about Y?
• How can we test that?
• How can we work together to create progress?

Finding solutions is the core of problem-solving. Asking these questions will help you generate ideas and find strategies for quick fixes.

While you question and explore solutions with your team, make sure the ideas being generated are consistent with relevant goals and objectives (e.g. hitting success metrics, increasing customer satisfaction, closing deals with SQLs, etc). Only then will you arrive at expert solutions that get you the right results.

Questions for empowering your team

• What do you believe to be the core issue in this situation?
• In your opinion, how should we move forward?
• How do you want XYZ to turn out? What are your goals?
• What do you need from me?

Every team member is a source of valuable thoughts and innovative ideas. But, oftentime, people who have good ideas aren’t given the opportunity to contribute and they grow disengaged. Surveys show that globally only 15% of employees feel engaged in their work.

A great leader knows how to ask the right questions to uncover ideas and empower more people in the decision-making process. Research shows that the companies that know how to empower their teams develop employees who are happier, more engaged, and 40% more productive.

Asking empowering questions also encourages team members to become better problem-solvers themselves, creating a team of dynamic thinkers and confident do-ers.

Questions for organizing action

Once you’ve generated new solutions, you need to put them into action. These are some questions that help sales leaders set success metrics, delegate tasks, and organize action:

• How will we measure success?
• What steps do we need to take to get there?
• What piece of this will each of you own? What piece of this do I own?
• How and when will we reconnect to check progress?

Questions for learning and improving

• How can we prevent this from happening again?
• What could I/we have done differently?
• Where can I/we improve?
• What’s a key takeaway from this experience?

Great problem-solvers know that problems are prone to come back in full force if the root cause isn’t solved.

To prevent future hiccups, leaders should work collaboratively with their teams to optimize and improve their processes. Use these questions to help you reflect on what could be done differently and develop a roadmap for future success.

Key takeaways

It’s important to keep in mind that not every sales obstacle requires a holistic, multi-step approach. Smaller problems like a CRM inaccuracy or a missed deadline for a minor project might only require one direct question to the right person.

But no matter the size of your current problem, you can be sure that having top-notch questioning skills will result in better solutions and more self-assured problem-solvers across the organization.

Pro tip: Prevent problems before they ever arise with Apollo's end-to-end B2B database and sales intelligence engine. Check out our blog on five quick ways to begin in Apollo and sign up for a free account here.