Upskilling for Startup Founders

The upskilling industry is expanding at a phenomenal rate.

The 2020 World Economic Forum’s Closing the Skills Gap initiative pledged to provide 8.1 million people with upskilling or reskilling opportunities across 26 participating companies to eventually add $11.5 trillion to global GDP by 2028. Their ambitious Reskilling Revolution aims to boost the job prospects of some 1 billion people in the next 10 years.

Numerous innovative upskilling platforms have received business funding, including that raised $16 million in a business funding round led by New Enterprise Associates (NEA). Novel upskilling platforms such as Degreed and Skillup are offering a fresh new take on upskilling for everyone from startup founders to employees and C-level executives.

So what’s with the buzz around upskilling? And why should start-up founders let themselves get swept up in this tide of upskilling demand?

The Buzz Around Upskilling

The drive for upskilling is largely motivated by the need to add much-needed technological and technical skills to the global workforce. The World Economic Forum found some of the following areas to show the greatest skills deficits:

  • Automation
  • Cloud computing
  • AI and machine learning
  • Software development, coding, and programming
  • Digital and remote working skills
  • Productivity and process optimization
  • Data science, analysis, and engineering

Whilst these types of technical ‘hard skills’ tend to dominate demand for upskilling and reskilling, there are plenty of soft skills that are also heavily in-demand.

This report by Guy Berger, Ph.D. found that soft skills such as communication, teamwork, and leadership topped the demands of employers. Research by PSI discovered that 67% of employers consider hiring employees for their strong soft skills, even when hard skills were lacking.

Upskilling for startup founders isn’t as simple as adding hard skills to one’s resume. It’s about locating and learning the skills that add genuine value to oneself and the team in which they work – these could be hard or soft skills.

How Does Upskilling Apply to Start-Up Founders?

Founding a startup is fun, exciting, and intrepid, but also a bit perilous, especially if the founder is putting down a good deal of their own money as start-up capital and is going it alone for the foreseeable future.

Startup founders need to have a Swiss army knife of skills and the more tools they can add to it, the better.

Upskilling for startup founders should be viewed as an opportunity for growth, development, and progress, rather than a chore. Embrace the need for new skills and start planning and prioritizing what skills you’ll need to learn and upgrade to make your business a success.

As the old adage suggests, if you fail to plan, then you plan to fail.

So where do you start? Upskilling for startup founders starts at the beginning – with planning.

Upskilling Your Planning and Organizational Skills

There are many tasks to complete when founding a startup. Some of the main tasks are establishing the business’s aim, its goal, products, services, and USPs. These initial tasks and processes as well as any forthcoming business activities require organization and planning.

Upskilling for startup founders

Planning and organization is the perfect target for upskilling. Scrutinize your skills in the following areas:

  • Setting goals; are you using SMART goals that are specific, measurable, aspirational, realistic, and time-bound? Revisit your goals and ensure that you allocate them a reasonable time frame for completion. Progress is there to be measured, so whether you’re looking for more leads, web traffic, sales activity, social media engagement, or something else, ensure that you’re capturing some sort of metric that can help you gauge progress.
  • Time management; how much time do you dedicate to the startup, and on what activities? It’s easy to mismatch the time spent on different business tasks, especially if you’re wearing lots of ‘different hats’. For example, you might be a marketing whizz but need to upskill your sales funnel tactics to convert marketing leads into sales. Manage your time to tip the scales towards practicing the skills you lack rather than those you’re already confident with.
  • Productivity; are you leveraging productivity tools and scheduling software? (Google’s GSuite of apps is the go-to but there are loads of options, e.g. Notion, Trello, Monday, Jira, ClickUp, etc). These tools are there to scale with you if you start to employ or collaborate with others. Learning to wield productivity and scheduling tools will unlock valuable time and money savings.

Upskilling Your Leadership and Management Skills

Harvard Business Review surveyed 141 HBS alumni start-up founders and compiled the most important skills.

Leadership and team management came 2nd and 4th respectively, with respondents citing that they often found it difficult to communicate their vision, motivate team members to invest in their ideas, and cultivate a positive working environment, especially when working with remote teams.

Upskilling for startup founders

  • Mentoring; the role of managers and leaders in modern business is more angled at mentoring. Team members need the support they need to do the job – this is preferable to micro-management and simply telling people what to do without some sort of conversational discourse. Learn how to angle your management skills towards mentoring – this will allow your team members to express their creativity – their suggestions might be of great benefit.
  • Communication; learning to be a better communicator is fundamental to managing a team. Delegation is also crucial – the key is to communicate tasks clearly and remaining open to explaining things people don’t understand the first time around. There are huge volumes of self-help and learning resources on the topic of communication, including this Amazon bestseller that regularly crops up in business reading lists.
  • Inspiration and enthusiasm; people will be able to invest in your idea if you’re inspired and enthusiastic about it, even if they do not necessarily share your end goals. Cultivate leadership skills and enthusiasm for your projects – it’s infectious.

Upskilling Your Technology Skills

The emerging technology skills gap is partly what caused upskilling and reskilling demand to rise in the first place. An EU-commissioned study found that until 2030 at least, the fastest-growing skills demand will be in IT and programming with a demand increase of 69% in the US and 65% in Europe.

Upskilling for startup founders

HBR found that product management, product design, and engineering management were frequent problems in startups.

  • Web design and management; this is a huge topic, but in broad terms, startup founders should look to upskill their website management skills so they can audit their website, make changes themselves, or communicate tasks to team members. The aim is a technically slick, SEO-optimized website with a solid UI and UX. Even if you’re hiring others to build and manage your website for you, you’ll need to learn key terminology and ideally be able to audit the technical and search performance of your site.
  • Marketing technology; digital marketing is center-stage when it comes to getting your startup out there and startup founders should always look to upskill their digital marketing knowledge. That means obtaining a foundational knowledge of key technologies and terms – know your CTAs from your CTRs and your PPC from your organic marketing. Find ways to target and re-target customers with ads, collecting behavioral data and customer data to enhance marketing and sales efforts.
  • Data skills; founders that harness data are more successful than those that don’t, according to McKinsey. Data is a huge topic in itself – startup founders should learn to work with the data they’re already collecting, e.g. their leads, sales, web traffic, etc. Make use of CRMs to log leads and analyze deals, use Google Search Console and Google Analytics to get to grips with measuring web traffic and audiences. HBR also found that learning to develop customer personas, A/B testing, product design and usability, personalization, and onboarding were all strong choices for upskilling.

Upskilling Your Sales Skills

The HBR survey ranked sales skills as 5th on their priority skills list for startup founders, making sales skills an excellent choice for upskilling for startup founders. Sales do not come naturally to everyone, but it’s not rocket science and anyone can learn how to better their sales techniques. The costs of hiring a sales team are also high, so upskilling and self-coaching here can save a lot of money.

Upskilling for startup founders

  • The sales funnel; an understanding of the sales funnel changes the way people view sales. The basic 4-stage sales funnel comprises Awareness, Interest, Decision, and Action (AIDA). The general idea is that potential customers progress in a journey from being aware of your brand to showing some initial interest, fostering that interest, and then deciding to buy. Upskill your knowledge of how the sales funnel works, you might be allocating far too much time to top-of-the-funnel marketing efforts without then taking those leads and nurturing them towards sales.
  • Pitching and direct messaging; pitching is a tricky area for those that don’t take naturally to sales, so learning how to pitch both in-person and on-call is an important area to upskill for founders that are looking to make deals and sell products. There are tons of free sales coaching sessions on YouTube. Consider recording your calls and reading back on past conversations to analyze what happened, why, and what you can improve upon for the future.
  • Lead generation and prospecting; prospecting is the art of finding leads. In a B2B space, this involves networking at events and conferences, prospecting from LinkedIn, building a social media presence, etc. In a B2C space, it’s more of an arm of marketing and focuses on finding those who have displayed an interest in your brand and products and turning them into customers. Upskill on prospecting techniques, for example, some CRMs like Pipedrive have built-in prospecting tools for locating contact details from LinkedIn or search engine results pages.

I Know What I Need to Upskill, But How Do I Go About It?

If you’ve identified some skills to upgrade then that’s great, but how do you go about upskilling?

As mentioned earlier in the article, there are platforms designed specifically for upskilling like Workera, designed more for data and AI, and Degreed, a more general upskilling platform for business.

But, upskilling really just requires founders to dedicate some of their own time to honing their skills and most importantly, learning new skills, some of which might be completely alien to them.

No matter what skill you identify you need, the internet will provide you with everything you need to learn it. Books are also great and can open the mind to all sorts of new topics on everything from data science and engineering to sales, leadership, time management, self-discipline, design, and much more.

Upskilling for startup founders, or anyone else for that matter, is both a personal and professional journey towards greater knowledge, enhanced skills, and a wider range of abilities. As they say, knowledge is power, power that can be channelled towards your startup.


My mother in law loves to sew.

A few years ago she asked me how to set up an online store.

She wanted to sell fancy throw pillows she was making.

I gave her very basic steps. Enough to get started (I don't know much about ecom).

A few weeks later she showed me her site. It

Everyone wants “yes.”

But they don’t wanna pay the price.

100 Nos is the price of one yes.

You can get as many as yeses as you damn well please as long as you’re willing to pay the price.

I was sad to learn that Charlie Munger died today at age 99.

What a life.

He would likely roll his eyes and argue that none of us should be too surprised, based on the actuarial tables, but we’ve lost one of the 20th century’s greatest investors and businessmen.

Chris and I

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