Building a Training Calendar for Teams

Can you see the sign just behind me? It says: "YOUR FAMILY IS EXPECTING YOU HOME TONIGHT" I saw it on the gate to a building site, on my way out of London City Airport. It utterly stopped me in my tracks. The sign was from a construction company, 8build and though it was clearly aimed at site workers, it stood out as a brilliant piece of communication that contains a wider lesson. Health & Safety messaging is often serious, procedural, and repetitive. Wear goggles. Watch for moving machinery. Fill out the form. Important? Absolutely. Memorable? Not always. And that's a problem. Because on building sites there is a phenomenon called Alarm Fatigue. It essentially means that if you work on a building site you can quickly become so desensitised to the beep beep beep of a large earth-moving diggers reversing that you tune it out. Which if you're standing behind one can have nasty consequences. The same phenomenon occurs in hospitals where monitoring machines sound alarms so frequently that nursing staff start to ignore them - which can be similarly harmful to human health. But the "family" message reframes the issue entirely. It isn't about the rules. It is about the personally-relevant reason to follow them. In a world where we're bombarded with signs, warnings, checklists and compliance notices, it's a powerful example of how to have people re-engage with boring but important signals. Imagine how other organisations could transform their tired messaging using this approach: Instead of "Please wash your hands" in hospitals, signs that read "Your next patient is counting on these hands being clean" Rather than "Back up your data" IT reminders, companies could use "Your best work deserves to survive a coffee spill" Instead of "Confidentiality agreement required" in client meetings, say "The trust our clients place in us begins with this signature" Rather than "Remember to schedule your annual review" in HR communications, remind your teams that "Your next promotion depends on a conversation we haven't had yet" An imaginative reframe can shift focus from dull procedures to clear purpose, and from reluctant compliance to consequences that matter personally. The sign at City Airport was a lesson about how reframing language inventively can have more impact on behaviour than almost anything else. What stale language in your organisation is no longer being heard? Are there critical messages for your teams, customers or suppliers you could refresh and reframe today? (And, hey, don't forget to stay safe: our families are expecting us ALL home tonight.)

Upskilling Strategies: Yesterday we looked at the Upskilling for business success and today we're going to look at customizing learning pathways for your Tech team. In today’s tech landscape, a one-size-fits-all approach to training just doesn’t work. To build a high-performing, future-ready tech team, upskilling programs need to be personalized and role-specific. 🔍 Start by assessing your team’s current skills: Use skills assessments, 360-degree feedback, and project performance reviews to understand the strengths and gaps within your tech teams. 🔑 Tailor learning pathways to meet the needs of specific roles within your organization. A few examples: ·       Cloud Engineers can benefit from certifications and training in platforms like AWS, Microsoft Azure, or Google Cloud. ·       DevOps Teams should focus on tools like Docker, Kubernetes, Jenkins, and CI/CD pipelines to streamline workflows and improve collaboration. ·       Cybersecurity Specialists need continuous learning in threat detection, encryption, and certifications like CISSP or CEH. ·       Software Developers could advance their skills in languages like Python or Java, or explore microservices and API development. 🎯 Personalization matters. When you align learning paths with individual roles and career goals, your team is more engaged and motivated, and the impact of upskilling is much greater. To create a successful upskilling strategy: ·       Set clear development goals based on current and future business needs. ·       Leverage e-learning platforms that offer customizable learning paths and assessments. ·       Encourage mentorship and peer learning to reinforce new skills within the team. ·       Investing in personalized learning paths doesn’t just future-proof your workforce—it drives innovation, improves retention, and keeps your tech teams agile and ready for the challenges ahead. Are your upskilling programs tailored to the unique needs of your tech team? #upskilling #personalizedlearning #techtrends #cloudengineering #DevOps #cybersecurity #continuouslearning #workforcedevelopment

How long should your onboarding program for SDRs be? I’ve now either trained or onboarded 1000+ SDRs in my career. I’ve built onboarding programs that were 1 week long, and more comprehensive programs that were 4 weeks long. Here’s what I’ve learned: 1. People don’t learn by being overloaded with documentation and videos upfront. 2. Onboarding doesn’t need to just happen in the first few weeks. Breaking down concepts in “micro lessons” over a period of time is more helpful. For example, if you sell 5 use cases, your SDRs don’t need to learn all 5 use cases in the first few weeks of onboarding. Let them master 1-2, focus on those prospects then unlock other personas. 3. People don’t retain information unless there is a continuous learning & re-enforcement loop You SHOULD set up weekly 1-1s, weekly calls reviews and power hours with reps from week 2 IMO. 4. Let SDRs learn on the job. Let them know it’s OKAY to fail. It’s okay to have some role playing up front. In fact, I recommend it. But don’t focus on this TOO heavily. They will butcher some calls and objections. Start practicing on Tier C accounts, don’t put new SDRs on the best accounts right away. With various AI sales enablement platforms like GTM Buddy, you can feed your SDRs real-time content, battlecards and learning as they are actually doing their job. It helps A LOT when it comes to actually learning and retaining information. My recommendation? Make your “official” onboarding for SDRs 1 week long. Include the following: 1. Upfront contract setting expectations for both manager and SDR 2. Day in the life of your Key Personas (Start with 1-2) 3. Main Problems you solve for  4. Basic platform functionality and how it solves problems for personas 5. How to structure your day / manage your time 6. Email / Copy Lessons 7. Cold Calling Lessons + Scripts 8. Using LinkedIn as a channel 9. Role Plays + Certifications for Email, Calls, LinkedIn 10. Overview of critical systems / tech stack Then focus on CONSTANTLY re-enforcing these. #sales #outbound

The best sales managers I know all have the same problem: not enough hours in the day. I watched a VP of Sales spend six hours this week role-playing with his team. Smart guy. Great leader. But those six hours barely scratched the surface of what his reps needed. Here’s the truth: The average sales manager spends 4–6 hours per rep per month on role plays. Ten reps = sixty hours of manager time. And that’s still nowhere near enough practice for reps to master their craft. Kyle Norton at Owner.com figured this out. Cut ramp time by 25% and gave his reps 10x more practice. How? He scaled coaching with AI that never runs out of time. *** The Multiplication Effect *** Sales development breaks down when: - Managers can only be in one place at a time - Role plays happen twice a month, at best - New scenarios get missed because there’s no time - Reps need 100+ conversations to get good—but only get 10 Smart teams are using Avarra to get reps conversation-ready in weeks, not quarters. When you add AI coaching: - Reps get unlimited, realistic practice 24/7 - Every rep gets personalized feedback - Win rates climb ~20% - Managers get their time back for real coaching Where it shines: → Rapid onboarding: new hires productive in their first month → Cross-sell readiness: mastering new talk tracks before going live → Launch enablement: everyone nails new messaging from day one → Renewal prep: practice hard conversations before they happen *** The Time Math That Matters *** Your managers are doing heroic work with limited time. But what if every rep got 50 practice conversations this month instead of two? What if managers could focus on deal strategy instead of basic skills? What if new hires ramped in three weeks instead of three months? More practice → better conversations. Better conversations → higher close rates. Faster ramp → revenue faster. Manager time freed up → more strategic impact. Your managers are already giving everything they’ve got. Give them tools that multiply their impact instead of adding to their plate.

If I was onboarding 5 new SDRs, here's exactly what I would do to guide them to exceed target in 90 days. Step 1: Learn the industry FIRST This is the most important step and most companies skip it. You can be subpar at prospecting and still do well if you deeply understand your buyers. Who are they? What keeps them up at night? How do they make decisions? What's the industry makeup? I remember reading every single article on VP of Marketing + CMOs when I worked at Terminus so I knew the lingo. When you know this, your conversations become 10x easier. Step 2: Set up their LinkedIn profile Now that they understand who they're talking to, let's make sure their profile reflects that. The question every rep needs to ask themselves is... How do we position our profile as someone worth responding to? I would immediately remove your job title from your profile and make the headline outcome focused. Think landing pages, not resume. Step 3: Get comfortable with the tech (but only 3-4 tools) I'm starting to believe you shouldn't give new reps all the tools at once. Start them with the basics: ↳ Sales engagement tool ↳ Data tool ↳ CRM That's it. Master those first. As they get better, they unlock new tools. As leaders, I think we need to have all SDRs master the fundamentals of these three tools so that the other tools are easier to use. Step 4: Creative prospecting Once they're comfortable with the basics, now we layer in video prospecting, voice notes, and creative outreach. I remember as an SDR, once I got the cold calling down I could easily translate those skills into more creative prospecting. This is where they start standing out from everyone else in the inbox. Step 5: Memorize 3 customer stories When I was an SDR manager, I told my team.. everyone needs to memorize 3 customer stories. That's it. Just 3. When you're on a call and you can reference a real story about someone like them... the conversation shifts. That's how you create relevancy by sharing a real point of connection they can relate to. These 5 things in the first 90 days will set your team up for success. P.S. Which step does your team need to focus on most?

This week, I facilitated a manager workshop on how to grow and develop people and teams. One question sparked a great conversation: “How do you develop your people outside of formal programs?” It’s a great question. IMO, one of the highest leverage actions a leader can take is making small, but consistent actions to develop their people. While formal learning experiences absolutely a role, there are far more opportunities for growth outside of structured settings from an hours in the day perspective. Helping leaders recognize and embrace this is a major opportunity. I introduced the idea of Practices of Development (PODs) aka small, intentional activities integrated into everyday work that help employees build skills, flex new muscles, and increase their impact. Here are a few examples we discussed: 🌟 Paired Programming: Borrowed from software engineering, this involves pairing an employee with a peer to take on a new task—helping them ramp up quickly, cross-train, or learn by doing. 🌟 Learning Logs: Have team members track what they’re working on, learning, and questioning to encourage reflection. 🌟 Bullpen Sessions: Bring similar roles together for feedback, idea sharing, and collaborative problem-solving, where everyone both A) shares a deliverable they are working on, and B) gets feedback and suggestions for improvement 🌟 Each 1 Teach 1:  Give everyone a chance to teach one work-related skill or insight to the team. 🌟 I Do, We Do, You Do:Adapted from education, this scaffolding approach lets you model a task, then do it together, then hand it off. A simple and effective way to build confidence and skill. 🌟 Back Pocket Ideas:  During strategy/scoping work sessions, ask employees to submit ideas for initiatives tied to a customer problem or personal interest. Select the strongest ones and incorporate them into their role. These are a few examples that have worked well. If you’ve found creative ways to build development opportunities into your employees day to day work, I’d love to hear what’s worked for you!

Are you planning your 2026 product training strategy yet? Most companies treat team development like emergency room visits, only when something's broken. But the best product organizations are already mapping out next year's skill development alongside their product roadmaps. Q4 is the perfect time to get strategic about this because when you plan a full year ahead, you can align skill building with your actual product challenges. If you need to launch in new markets, your team can master market research before they need it. If you're rolling out AI features, get them up to speed on tech fundamentals now, not when deadlines are looming. I've seen too many companies scramble for quality training when skill gaps become urgent. The options shrink, the costs rise, and your team spends months playing catch-up instead of driving forward. The complexity of product work isn't getting simpler. Your teams need everything from user research to market analysis to technical fluency. But when you plan ahead, you can build these capabilities systematically rather than reactively. At Product Institute, we're seeing smart organizations lock in their 2026 development plans now. They're treating upskilling like the strategic investment it is, not an afterthought. How does your company approach product team development? Strategic planning or emergency response?

🚨 Most leaders believe their teams are trained. But have they actually understood the content? There's a dangerous gap between distributing safety information and knowing your team can act on it — especially across language barriers, cultural communication styles, and power dynamics that make people reluctant to say "I don't understand." In my latest article, I unpack why this gap exists, what it costs, and exactly what to do about it. Here's what you'll walk away with: ✅ The real reason "Does everyone understand?" gets a silent yes — even when it shouldn't ✅ Why compliance checkboxes can create a false sense of security on multicultural teams ✅ 4 practical strategies for making safety communication genuinely accessible across languages and cultures ✅ The leadership mindset shift that separates good intentions from real impact This one is for every team leader who has ever walked away from a training session assuming comprehension happened — when all that really happened was information was delivered. 👇 Click the link to read the full article. #MasteringCulturalDifferences #GlobalLeadership #CrossCulturalCommunication #InclusiveLeadership #WorkplaceSafety #CulturalCompetence #MulticulturalTeams #LanguageAccessibility 

The winner for best slides at #LeadDevBerlin came from 🐱 Denise Yu from HashiCorp, who spoke about levelling up your entire team, and avoiding “superhero” development. ⬇️ “Level Up the Whole Party, Not Just the Hero” • Uses the Pokémon metaphor of training one Pokémon vs. a collection: good leadership is a series of repeated and consistent behaviours. A well-balanced team is more effective than a single code hero. • Final Fantasy VII team reference: each team member has their own strengths, and 3 out of 4 would suffer if forced into one mould. • A balanced team includes varied demographics, thinking styles, experience levels, motivators, etc. • Take stock of your desired end state: your team should include a good mix of styles like teachers, specific tech stack expertise, carers, doers, etc. Create a map of needed expertise. • Expertise: “Novices only see what is there; experts can see what is not there” (Gary Klein quote). • Re: Expertise, Denise likes to ask: “How much cursed knowledge do you have?” (knowledge you gained without wanting to! 😅). • Theory of Proximal Development: do tasks you can accomplish with some assistance (not tasks you can already do or ones you can’t complete at all). • Identify where an engineer is now and where they want to be; map their progression with steps that involve only changing one thing at a time. • Go through a career matrix with each engineer, assessing their self-evaluation of abilities; set goals based on agreed gaps. • Use everyday decisions to incrementally advance your team. • Work distribution options: free-for-all (everyone picks tasks) vs. assigning every individual ticket. Best option: create norms around ownership, with initiative-based leads who can self-organise. • Assigning work is like giving experience points to different team members (RPG metaphor). • Repeatedly giving one star member the same tasks means losing opportunities to develop that skill in others. • Be willing to accept short-term slowdowns to achieve long-term speed and a balanced distribution of skills and expertise. (notes cleans up by ChatGPT) —— I loved Denise’s video games metaphor and found it enjoyable and impactful. I am to always lift up the team as well as the individual, but her reminder to not just lean on the same team member for the same tasks was something I will definitely carry forward. Thank you Denise for a great presentation!! Unfortunately I didn’t get many photos of her amazing Charmander slides but suffice it to say they were awesome! #EngineeringManagement

A lot of time and money goes into corporate training—but not nearly enough comes out of it. In fact, companies spent $130 billion on training last year, yet only 25% of programs measurably improved business performance. Having run countless training workshops, I’ve seen firsthand what makes the difference. Some teams walk away energized and equipped. Others… not so much. If you’re involved in organizing training—whether for a small team or a large department—here’s how to make sure it actually works: ✅ Do your research. Talk to your team. What skills would genuinely help them day-to-day? A few interviews or a quick survey can reveal exactly where to focus. ✅ Start with a solid brief. Give your trainer as much context as possible: goals, audience, skill levels, examples of past work, what’s worked—and what hasn’t. ✅ Don’t shortchange the time. A 90-minute session might inspire, but it won’t transform. For deeper learning and hands-on practice, give it time—ideally 2+ hours or spaced chunks over a few days. ✅ Share real examples. Generic content doesn’t stick. When the trainer sees your actual slides, templates, and challenges, they can tailor the session to hit home. ✅ Choose the right group size. Smaller groups mean better interaction and more personalized support. If you want engagement, resist the temptation to pack the (virtual) room. ✅ Make it matter. Set expectations. Send reminders. And if it’s virtual, cameras on goes a long way toward focus and connection. ✅ Schedule follow-up support. Reinforcement matters. Book a post-session Q&A, office hours, or refresher so people actually use what they’ve learned. ✅ Follow up. Send a quick survey afterward to measure impact and shape the next session. One-off training rarely moves the needle—but a well-planned series can. Helping teams level up their presentation skills is what I do—structure, storytelling, design, and beyond. If that’s on your radar, I’d love to help. DM me to get the conversation started.