When a company hires or promotes its first sales manager, expectations run high, but clarity can be low. In this episode of Two Tall Guys Talking Sales, hosts Sean O’Shaughnessey and Kevin Lawson unpack what the first 90 days should look like for a new sales leader. Whether you’re a CEO onboarding a new manager or that manager stepping into the role themselves, this discussion provides practical guidance on setting realistic expectations, building trust, and establishing the foundation for long-term sales success and revenue growth.

 

Key Topics Discussed

• Setting Realistic Expectations as an Owner (02:00 )
  Kevin explores how CEOs should frame success during the first 90 days, emphasizing the importance of patience, trust-building, and understanding that sales management transformation takes time.
  
  

• Avoiding the “Fix This First” Trap (06:30 )
  Sean cautions business owners against dumping old personnel problems on new leaders, explaining why cleaning up someone else’s mess undermines early business acumen and trust.
  
  

• Building Relationships and Learning the Business (08:30 )
  Sean shares tactical advice for new sales managers: conduct one-on-ones, ride along with reps, and build rapport across departments, marketing, operations, and finance, to master internal sales processes and interdepartmental alignment.
  
  

• Understanding Internal and External Tools (11:12 )
  Kevin discusses discovering hidden tools and levers, people, systems, vendor programs, or product configurations that can immediately improve team performance and value-selling opportunities.
  
  

• Repackaging and Aligning Offers to the Market (12:30 )
  The hosts outline how sales leaders can rethink product structures and messaging to better serve customer needs, thereby improving revenue management and profitability.
  
  

 

Key Quotes

“Trust is a currency. It has to be earned by customers, by salespeople, by peers, and you can’t buy it in the first 30 days.”,  Kevin Lawson (03:00 )

“Don’t make your new sales leader the bad guy. If there’s a tough personnel decision, handle it before they start.”,  Sean O’Shaughnessey (07:00 )

“Learn your company inside and out. If you don’t know who runs manufacturing or how the supply chain works, you can’t lead your salespeople effectively.”,  Sean O’Shaughnessey (10:00 )

“You might have 20 products, but 100 possible solutions. The smart leader finds ways to repackage and sell in ways the customer actually values.”,  Kevin Lawson (13:00 )

 

Additional Resources

• Episodes on sales onboarding, marketing alignment, and ideal customer profiling (ICP) were referenced throughout the conversation.
  
  

• Explore more insights and tools for sales leaders at b2b-sales-lab.com.
  
  

 

A Significant Actionable Item from this Podcast

Create a 90-Day Integration Plan.
If you’re a new sales manager, spend your first month listening and learning. Conduct one-on-ones with every salesperson, schedule cross-department meetings, and document what each function needs from sales. In the second month, identify process gaps and start designing improvements. By the third month, implement one or two visible wins, such as improving forecasting accuracy or clarifying sales messaging, to demonstrate value and build momentum.

 

Summary

Your first 90 days as a sales leader can define your entire tenure. Sean and Kevin reveal that success isn’t about quick wins, it’s about developing relationships, earning trust, and understanding the organization’s systems before making bold changes. For CEOs, this episode provides a masterclass in setting expectations. For new leaders, it’s a roadmap to transition from individual contributor to strategic operator.

Listen to this episode of Two Tall Guys Talking Sales to learn how to step confidently into leadership, master sales strategies, and drive lasting revenue generation through purposeful sales management and business acumen.

To understand if your company is doing a great job in sales, take this quick and easy assessment:

Sean's Assessment: https://newsales.expert/b2b-sales-capability-assessment/

Kevin's Assessment: https://salesxceleration.com/sales-agility-assessment/?locationid=28995327

 

B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It’s a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com

 

You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/

 

You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/

 

You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin

 

You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/