The Half-Life of Productivity Tools

Most of your company’s problems are people problems. It’s not that the people themselves are the problems (usually). Rather it's the relationships between people that causes issues. Differences in communication preferences, working styles, emotional maturity and motivations can act as friction points, impacting productivity. These matters often go unnoticed or unacknowledged.

From my experience, many companies don’t think of their troubles as human-centric ones that require interpersonal skills as solutions. Instead, they believe the answer to their output woes lies in an updated process, performance KPI or new-fangled productivity software. There is a belief that a *thing* can solve their problems. Better yet that thing will provide a dashboard with metrics that show how well collective performance is improving through # of docs shared, messages sent and hours logged! Productivity is treated as an engineering query to be solved, with a binary and technical solution. This is rarely the case. When people are involved in an output, human-nature always plays a role in the delivery.

John Cutler @johncutlefish

The fact that companies are sociotechnical systems not distributed computing systems is deeply bothersome to some engineer founders.

However, sometimes a new productivity/collaboration tool is exactly what’s needed. I started my career in tech as an Implementation Consultant and saw first hand how upgrading the tools available to teams to get their work done can have a positive impact on productivity and morale. Using legacy systems can have a negative business impact. Just ask Southwest Airlines. That being said, having implemented several new collaboration products at startups, I know that software isn’t a panacea. Productivity tools tend to have a half-life. X-period post deployment their effects start to wear off. Sometimes this is due to scaling which has introduced a new set of growing pains. More often than not, it is due to the underlying people issue not being resolved.

Productivity software costs can really add up. Before investing in a new solution, it's worth considering the underlying problems, alternative approaches and potential changes required in the business to make it a successful endeavour.

Common Problems

“We can’t keep track of everything that’s happening in the company. There is too much noise. We need a new tool to centralise everything so that we’re always up-to-date on the latest happenings for each team / product / project.”

Over-communication, under-communication, document sprawl. We’ve all likely experienced these at some point. Not knowing where to find an update or being able to quickly identify what’s a must-know vs nice-to-know can lead to a sense of frustration, anxiety and overwhelm at times. Before rushing to implement yet-another-SaaS-solution there are a few points to consider.

This may actually be a positive sign of:

• Transparency: You may be operating in an org that values openness and actively aims to break down silos. 

• Collaboration: Teams may readily be engaging with each other and sharing information.

• Momentum: The volume of comms required scales with growth.

You may actually be trying to solve for:

• A sense of control: Startups can be ambiguous and chaotic. Trying to keep on top of every detail happening within the org may feel like you’re maintaining order, but it is rarely effective or scalable. Can be a symptom of trust issues.

• Lack of clarity in role: If it’s unclear what you are directly responsible for knowing in depth vs what is acceptable to delegate it can create a sense that you’re never getting the right level of information to succeed in your role. Can be a symptom of poor management.

• A resource gap: At a certain stage, companies usually need to hire people to help maintain the flow of information across orgs. This can take the form of internal comms, Product Ops, Chief of Staff amongst others. Can be a symptom of org structure issues.

Common go-to-solutions:

• Long-form comms software (e.g. Threads, Twist), wikis/intranets (e.g Notion, Workplace), comms aggregators (e.g. Shift, InVision), building custom internal tools.

Before implementing a new tool, consider trying:

• Implementing comms norms: Providing guidance on which existing tools to use for different types of comms can help bring order to the chaos. Ensure important updates are shared in a consistent manner (same frequency, same location). These changes should help with curation.

“Nothing ever gets delivered on-time or in the right way. We don’t know why. We need new project management and goal setting tools to ensure things get done. It’ll hold people accountable!”.

Projects are delayed. Unforeseen issues crop up right before launch. Goals are consistently missed. Some teams complain that they are overburdened with requests. Others complain it takes too long to ship anything.

This may actually be a positive sign of:

• Ambitious goals: Teams may be aiming high and delivering a lot of valuable work. However, this is not appreciated due to unrealistic goal setting caused by estimation issues.

• Teams are focusing on doing the work: Status updates take time. Teams may be focusing on delivering rather than reporting.

• Momentum (again): The more you grow, the more work (usually) gets created.

You may actually be trying to solve for:

• Prioritisation issues: Teams are stretched. Less important work is being done at the expense of more critical tasks. New projects and working groups are regularly getting launched yet rarely deliver. Nothing is important when everything is important. Helping teams narrow focus can result in greater output.

• Accountability issues: A lack of ownership causes work to linger in the WIP ether. Blame culture abounds. Ensuring that each project, product or KPI has one person of appropriate seniority accountable for delivery can help ensure things get done, or that at least there is a clear understanding of blockers.

• Strategy issues: Sometimes work isn’t delivered because teams don’t know what direction they should work towards or that direction keeps changing. What success looks like may be unclear. Sometimes it’s a lack of faith in the company’s vision. Ensuring teams deeply understand and are bought into the strategy can help improve velocity.

Common go-to-solutions:

• Project management tools (e.g. Asana, Jira), OKR trackers (e.g. Lattice, Gtmhub), a trusty spreadsheet, building custom internal tools.

Before implementing a new tool, consider trying:

• Understanding the root cause: Work is rarely not delivered because people didn’t provide enough status updates. Most workplaces tend to over-index on this process. Instead, it is likely that there is another factor at play which is preventing teams/individuals from delivering. This could range from lack of clarity on who's accountable, internal bureaucracy, problematic team or management dynamics, a culture of underperformance and shirking responsibility, lack of resources or skills, external circumstances or a lack of buy-in. Understanding the ‘why’ can prevent the cycle from repeating.

“Our company is siloed. Teams don’t talk to each other or share relevant insights about customers. We need a tool to open up communication and capture all this customer information so we can act on it.”

Sales aren’t happy with what Product are building. Support is inundated with the same bug queries who’s fix never seems to make it off the backlog. Customers churn and nobody knows why. Or worse, they churn for entirely preventable reasons.

This may actually be a positive sign of:

• Solid ICP focus: Teams may be focusing on serving a subset of customers exquisitely at the expense of others. There is strong conviction in the problem being solved and building for target customers.

• Ambitious roadmap: As much as we may wish it, not everything can be built at once. Teams may be focusing on larger longer term opportunities at the expense of existing ones.

• Momentum (yes, again): The more you grow, the more requests you’ll receive from customers.

You may actually be trying to solve for:

• Prioritisation, accountability and/or strategy issues: See above.

• Lack of cohesion: GTM strategy and customer outcomes cannot be managed by one single function or C-suite leader. It requires input from sales, customer success, marketing, product, operations and others. Ensuring there is good cohesion amongst the senior leaders of each function, and ensuring that org structures are built in a way that simplifies decision making and reporting structures can help ensure that there is alignment on customer and company priorities.

• Lack of data: Sometimes companies don’t know what profile of customers are using their products, why usage trends are changing and what the issues and opportunities are. Investing in capturing and collating qualitative and quantitative customer data can help ensure customer needs are better understood.

Common go-to-solutions:

• There are few products that solve for this issue (although I know of at least one being built in stealth). Typical tools used to solve this are customer success platforms (e.g. Gainsight, Planhat), roadmapping software (e.g. Productboard, Pendo), product request forms integrated into CRMs and many internal meetings.

Before implementing a new tool, consider trying:

• Developing a user-centric culture: It’s amazing how many companies lose sight of their customer, whether it’s due to an excessive focus on costs/profits, internal politics or by being distracted by status games. Creating a culture where every leader and their teams understand the company mission, their role in the customer journey, and their responsibilities for ensuring good outcomes can help ensure that the customer experience is always being considered.

Additional Considerations

Tech-folk can have magpie tendencies, getting overly excited by shiny new tools which promise to do things BETTER, FASTER, CHEAPER! Before splashing out on the latest trend on Product-Hunt for your team it’s worth asking yourself these questions:

• Do you expect this new product to meaningfully change behaviour, performance and / or communication or at best incrementally improve them? If incremental, is it worth the effort and expense?

• Is the problem a tools problem or a how-tools-are-used problem? Can you use existing products to achieve your goals?

• Are you upgrading or downgrading the tools being provided to your teams? How could this impact the work being delivered?

• Will this tool decrease the effort required to get things done? Is there a danger teams will spend more time focused on admin rather than delivery work due to this change?

• Are managers and leadership going to use this product or are they expecting teams to continue to provide updates in more manual ways e.g. status slide decks, end of week emails? Which process/expectation/behaviour needs to change to prevent duplication of work?

• Are you trying to solve a cultural issue with a product? Is that truly possible or does this require more of a human-touch?

It may sound like I’m trying to talk you out of purchasing additional software. I’m not. Productivity tools can be great! Often companies fail to leverage them to their benefit. I’ve seen far too many examples of organisations vetoing the purchase of a £10k a year tool while then proceeding to hire a £60k a year employee who spends 50% of their time on work that would have mostly been automated or streamlined by investing in tech instead. However, I’ve also witnessed haphazard implementation of software that ends up not providing the benefits intended. Sometimes it’s an adoption hiccup that can be solved through training and the implementation of comms norms. Often, it’s a cultural issue that requires a non-technical solution. Knowing which problem you’re solving for is key.