Image Cover for Article Upskill or Bust: Transforming Your Digital Marketing Team

My digital marketing students come for two reasons. They want to get better at Digital Marketing, or their boss sends them to class. Salesforce research revealed that 59 percent of workers have had fewer opportunities for workplace learning since the pandemic.

Are you the boss or the self-directed student? I have seen hundreds of organizations fail to produce the change they desire. Please align first on the Why of Learning and then tackle the Leading (SEO, AI, Media Buying) and last How to manage it. 

Less Workplace Learning during the Pandemic

To upskill a marketing team effectively, I focus on Why first? 

Why is the student in my class at UNH? Then, What are the 2-3 three items they want to take back to their organization? Most of my students have demanding jobs and need to be highly efficient in getting to the practical marketing tactics that will impact next week. 

Business owners and managers often head into Upskilling by trying to learn too much too fast, and little ends up sticking with the day-to-day for your Marketing Team

How Do You Identify Skill Gaps in Your Marketing Team? 🧠

Upskills or Bust - Identifying Skill Gaps

Assessing Current Marketing Skills

The first step is to conduct a thorough audit of your team’s current abilities. I do this in two ways. The first step is a 30-minute interview with the team member, where I cover the following areas:

  • Can articulate a clear Multi-Channel Strategy
  • Precise customer Segmentation and ongoing regular data-driven Insight 
  • Effective Multi-Channel Brand positioning and storytelling
  • A recent demonstration of Drafting off of current trends or market moves (Reactive vs data-driven vs Automated)
  • Top 2% Execution per role (individual contributor, team lead, marketing manager, marketing director, VP, CMO, Owner, Board Member)
  • Testing and Creative Process
  • Data Analytics (GA4, User insights, statistical significance, platform metrics, attribution, iteration)
  • Metrics and ROI and clear links to business goals vs vanity metrics 
  • Marketing Automation (Reactive vs Organized vs Automated)
  • Partners in areas of weakness which augments the team with internal/external resources

Next, we get Loom out and see their actual marketing work in process. Just have your team send you a Loom (or your video tool of choice) of their current process as they do it. SEO keyword research sends a Loom. AdWords Camaping structure sends a Loom. Attribution deep dive sends a Loom. 

Very quickly, you can produce a simple spreadsheet matrix that identifies the strengths and weaknesses of your Marketing Team. 

Setting Upskilling Goals

Once I’ve established where my team stands skill-wise, I set clear upskilling goals that are SMART (Specific, Measurable, Achievable, Relevant, and Time-based). This involves pinpointing which skills will provide the most value to our business. For instance, if we’re lagging in digital analytics, a goal might be to have a certain percentage of the team proficient (as demonstrated in a Loom video) in Google Analytics within six months.

Aligning Skills with Business Outcomes

Finally, it’s vital to ensure that the upskilling goals you set are going to drive the business outcomes your company needs. This is where many managers get off track. They focus on the shiny digital marketing fad of the quarter (NFT’s 🤣) vs timeless marketing skills:

  • Content Creation and Storytelling
  • SEO and SEM
  • Data Analysis and Interpretation
  • Email Marketing and Copywriting 
  • UX, CRO, Landing Pages, and Testing
  • Video Production
  • Project Management
  • Marketing Automation and AI
  • Graphic Design and Color Theory
  • Competitive Marketing Intelligence
  • Digital Media Buying

What is your Time Budget for Team Upskilling? 🕰️

Time Budget for Team Upskilling


I make this mistake all the time. Even if I show someone how to do something, they still need to set aside time on the calendar to practice it. If you manage a team and don’t have the team set aside time on the calendar to get the practice repetitions in, they won’t improve in their execution. 

Cost-Effective Learning Strategies

I’m frugal, and our learning involves microlearning—short, focused training modules that can keep costs down and conveniently fit into my team’s busy schedule. We prioritize:

  • OnDemand Platforms: By leveraging online training resources, I can offer my team the flexibility to learn at their own pace.
  • Online and Hybrid Classes: At UNH and many other outstanding institutions, you can meet your peers and learn what is also working for them. 
  • In-House and External Expertise: Utilizing experienced team members as mentors is a resource-smart strategy, capitalizing on internal knowledge without always spending on courses. Ask your marketing peer who is crushing it on TikTok to chat about what is working for them on a 30-minute Zoom call.  
  • Free Digital Marketing Courses We Love for 2024 ⚡

Return on Investment in Marketing Training

We all have a CFO or business partner in our organizations who would rather cut the training budget. Just remind them of the expensive consultant or tool you had to buy because you lacked the in-house skills. We can’t be experts in everything, but Digital Marketing has been evolving at the fastest pace in the last 20 years. Keeping your team skilled is a high ROI activity vs obsolescence or the recent story of a client wasting $52,000 in a month because their team did not set up Adwords correctly!

How do I Upskill our Marketing Team? 📚

Upskills How do I Upskill our Marketing Team


  • Start with a 90-Day Learning Plan
  • Time Block your team’s Calendar
  • Embrace microlearning — Microlearning entails brief, targeted learning segments designed to meet a specific learning outcome. For instance, engaging in Marketing microlearning sessions can be particularly beneficial. These bite-sized educational units deliver focused, skill-specific knowledge that can be directly applied that day to marketing tasks. My team benefits from this approach, as it complements their busy schedules and provides actionable insights in short timeframes.

Balancing In-House Training and External Experts

For in-house training, I leverage the expertise within my team, encouraging knowledge sharing and peer-to-peer learning. This approach fosters a culture of continuous learning and strengthens the team dynamic.

  1. In-House Training:
    • Identify internal experts
    • Schedule regular knowledge-sharing sessions
    • Encourage mentorship programs

Concurrently, bringing in external experts offers fresh perspectives and specialized knowledge. These experts can provide valuable insights into current market trends, new strategies, and tools that may not be available internally.

  1. External Experts:
    • Curate a list of industry leaders, peers, and organizations relevant to your 90 Day Learning Plan
    • Organize workshops, lunch and learns, or guest lectures
    • Test microlearning opportunities via Zoom with Experts

Both strategies work in tandem to create a well-rounded upskilling experience for the marketing team, allowing them to stay ahead of industry curves and deliver superb marketing performance.

Advancing Digital Marketing Skills 💎

Alec, that works well if my team wants to learn the basics of digital marketing, but how do we master Advanced Topics?

That is simpler than you think. There are a small number of Top 10% practitioners in each area.

I ask three qualifying questions:

  1. Have they repeatedly done this advanced marketing topic? For example, I recently wanted to understand bleeding edge trends on the topic of “Parasite SEO” so I purchased two courses from gray/black hat SEO experts that consistently had verifiable results on this subject. 
  2. Do they have reviews from people or organizations I know and Trust? If not, keep looking. 
  3. Is the information current and up to date? Many courses I see are badly out of date with tactics that worked well years ago, but the algorithm has passed them by. 

Learning Leadership and Team Dynamics 🔼

Upskills Learning Leadership and Team Dynamics

The crux of upskilling a marketing team lies in leaders taking time to show that we are also going to class and learning regularly. When did you take your last marketing course? What did you share with your team over lunch and learn?

Professional Development

  • If you don’t demonstrate learning is a priority as a leader, the troops won’t follow
  • Have your own Learning Plan
  • Make a Time in the Calendar each month
  • Track metrics that matter to business outcomes to keep the funds flowing 

How do we do Upskilling with a remote team?

The shift to remote work has made collaboration tools indispensable for team bonding and efficiency in a digital environment. Therefore, I prioritize:

  • Consistent Communication Platforms: Utilizing tools like Slack, Loom, or Microsoft Teams for daily check-ins and updates.
  • Virtual Team-Building Activities: I find that activities such as remote lunches or group challenges help in maintaining team cohesion.

In each virtual meeting, I ensure that:

  • Clear Agenda: We use Notion meeting templates to set discussion points in advance and optimize meeting time.
  • Active Participation: I struggle with this but try to encourage every team member to contribute, ensuring their voice is heard.

Measuring the Impact of Upskilling 📈

Measuring the Impact of Upskilling

To ensure the investment in learning translates into meaningful business outcomes, I focus on evaluating the effectiveness of our training programs.

Tracking Progress with KPIs

When I measure the impact of upskilling initiatives in marketing, I concentrate on metrics and KPIs (Key Performance Indicators) that relate directly the teams marketing performance and business objectives. Here’s how I approach it:

KPI Baseline Target Current Status
Paid Ad CTR 2.5% 3.5% 3.1%
CS 3 Hour Response rate 80% 90% 85%
Landing Page Tests 1 per month 3 per month 2 per month

How We Use Notion for Continuous Learning

Notion is a key tool in our strategy for continuous learning and upskilling. This is how I integrate it:

  • Resource Centralization: I create a unified repository of marketing materials, learning resources, swipe files, micro courses, videos, and training guides that my team can access anytime, fostering an environment of continuous learning. Notion is very good at mixing many different types of content into something that is well-organized and pleasing to the eye.
  • Progress Tracking: By setting up individual and team pages, each member records their upskilling journey, documenting new skills learned and sharing insights.
  • Collaborative Learning: My team utilizes Notion’s collaborative features to share constructive feedback asynchronously so we don’t die by meetings.

By systematically measuring the impact of our upskilling efforts and continuously fostering a learning culture with efficient tools like Notion, I ensure my team is equipped with the tools to win. 

Focus you and your team on Why you want to learn, then Lead by assembling the Top 10% resources to help you practice the What and How. Strong businesses are built on adaptability. No area of your organization needs that adaptability more than your marketing team. With constantly evolving trends and tools, staying ahead of the curve is integral. To be better prepared for change, upskill your marketing team. After all, the key to navigating AI-driven change is having a team that’s ready for it.

UNH Class Email Header Marketing Alec 2

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