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Talent Management for Digital Transformation Part II: Training and Growing Your Current Staff

We’ve all heard the old adage, "your employees are your most valuable asset." But in the face of digital and operating model transformation – a time when adaptability and agility are prized traits – this notion comes with added importance, as well as newfound challenges. And as traditional job roles evolve, organizations need to button up their talent management strategy so that their digital-transformation talent can help build the future they envision.  

In part II of this series on talent management, I’ll break down the reasons why digitally-transforming companies should proactively invest in their existing talent pool and share best practices for nailing that endeavor. 

The Advantages of Cultivating Existing Staff

When it comes to cultivating talent within digitally-transforming organizations, or organizations shifting from a project-to-product mindset, it can be tempting to think about creating new teams from solely external sources. In reality, it’s not an either-or proposition. 

While external hiring is absolutely a natural part of transformation, today’s focus is on upskilling your current staff, which has advantages like:

  • Preserving institutional knowledge: Existing employees possess an intimate understanding of the company's DNA, history, and unique challenges. By upskilling them, you not only harness their expertise but also prevent the loss of critical insights that might occur with high staff turnover. 

  • Cost-effective benefits: Recruiting can be an expensive and resource-intensive endeavor. From advertising the position, conducting interviews, and onboarding, the costs can quickly accumulate. And in this market, positions can take time to fill, which can jeopardize team success when roles sit open for too long.

  • Boosting employee morale and loyalty: Demonstrating a commitment to employee growth sends a powerful message about your company's investment in its people. When employees see opportunities for development and advancement within their current organization, they are more likely to feel valued and motivated to contribute their best.

Setting a Talent Management Strategy Is Paramount

In the following sections there will be plenty of tips for cultivating your current talent, but all of it is predicated on the idea that you have already defined a desired future state for your transformation


It’s critical to get clear on what you’re trying to achieve and why. This will inform how you train and grow your current staff in a way that supports your vision for the future. Without this step, it’s like setting out for a roadtrip with no destination. Can you put some miles on the car? Sure. But you’re not likely to have a satisfying experience without some forethought to your destination. 

If you have not yet done this, do not pass go! Instead, check out Part I of this series to learn about the crucial inputs to consider when aligning talent with your organization's digital goals. 

Assess Your Talents’ Skills and Competencies

Before you can upskill, you need to get the lay of the land. And this is going to require a great deal of honesty and vulnerability, so be sure that you’ve set some ground rules with your teams and human resource partners. Evaluating peoples’ abilities can be a really vulnerable feeling, but if you frame it up intentionally it can shift the energy around the endeavor to help you achieve the outcomes you’re seeking.    

I recommend starting the process by looking at the common skills and competencies required for agile and product-led roles, as well as soft skills (the intangibles that don’t come across on paper but make a huge difference, like this trait that I always look for in product people). There’s been a ton of ink spilled on this topic (600M+ results on my last Google search), but try doing a scan of open product roles on LinkedIn, or review these articles, or this one. You’ll start to see trends emerge, and you’ll also start to see what is missing from your current workforce. 

The next step is to assess your teams against the skills and competencies you’ve assembled. This can be as informal or as formal as you’d like, but it’s essential that you explain the context of the assessment to your teams. They can’t think that this is a pass/fail situation – they need to be on board with the attitude that it’s really about identifying growth opportunities for themselves individually, and the company as a whole. 

During the assessment process, make sure you bake in moments for employees to express their career aspirations. What skills are they interested in growing? Are they curious about new roles? How do they see their position evolving? 

New skills can be learned, but curiosity is innate. And the curious people – the ones with a growth mindset – are the ones who will take you the furthest because they’re ready to lean in! 

Implement Training and Upskilling Programs for Talent

Once you’ve completed your talent assessment, you should be able to hold up the existing skill set against your desired skill set. From there, you can identify the gaps and start to build a bridge between the two.

And by “bridge” I mean a comprehensive training plan filled with learning and development opportunities based on your talent’s needs and the organization’s digital transformation goals.

There’s no one-size-fits-all model for this plan because training will be specific to your talent’s growth opportunities. 

For example, let’s say your staff scored high on discipline-specific fundamentals like agile, but are struggling with innovation and collaboration. A training to support that upskilling looks really different than a training aimed at more tactical skills, like building roadmaps and healthy backlogs.

Here are some options you can consider for implementing learning opportunities:

  • Offer both internal and external training programs on digital technologies and best practices. Partner with an organization that can teach a course to your staff on a desired topic. Find industry leaders doing workshops and trainings in your opportunity areas, or leverage the people who are excelling in those areas internally to create a training that brings others along for the ride. You don’t have to create everything from scratch, so find the right balance between internal and external resources to shape your program.

  • Everybody learns differently, so it’s critical to provide different formats that appeal to many types of learners. Give people access to online learning platforms and resources, offer workshops, organize opportunities for group study, create self-paced learning modules. The more options you make available, the more people you’ll bring along for the ride.

  • Support a culture of continuous learning by building training into an annual goal setting and personal development process. This is not a one-and-done endeavor, but an ongoing commitment that needs leadership’s support to take hold as a mindset.

Creating Opportunities for Employee Growth Within Digitally-Transformed Organizations

Training programs aren’t the only ways for people to learn. 

Find opportunities to challenge staff with assignments that encourage them to hone a new skill set, or offer cross-functional projects to help develop digital skills. You could even roll out an “exchange” program where you send someone out to another team, then bring them back so they can show what they’ve learned and implement news skills within their existing team.

I also recommend incorporating mentorship and coaching programs that support career development into your plan. This shows employees that you’re not only supportive of their upward mobility, but invested in the effort to get them there.

Finally, look for opportunities to recognize and reward employees for their contributions to digital transformation efforts. Give them the chance to present at an all-hands meeting, or lead a lunch-and-learn presentation on a topic or project they’ve been immersed in.

If You Build It, They Will Come

While external recruitment will surely be necessary to build your bridge to your future state, the strategic decision to invest in upskilling current staff should be taken seriously. It’ll help improve morale and retention rates, foster better cross-team collaboration, and promote skill sharing.

Closing the skill gap is an essential precursor to achieving a successful transformation, but it’s not without challenges. I’ll be talking more about how to overcome common talent pitfalls in Part III of this series, so send me a note with your questions and I’ll address them in the next installment.

In the meantime, here are a few more resources related to talent management that you can dive into: