Startup Strategy is a Beast — here’s how we keep Track and do the Planning with Software

When looking back and connecting the dots, I must admit that we’ve lost several months at Compass.To not being aligned in our strategy, not being accountable for what we’ve missed and missing an overview of what every team is really doing and achieving. 
Two teams on two continents with another team working on and in China quickly becomes a true weakness if not a threat to our venture and mission. 
My co-founder Alexander Bierling and I assessed six software tools — also considering the big ships Salesforce and SAP — to help us achieving our goals more constantly and with a software that kicks our ass when missing a KPI or coming up with an idea that has some sound but doesn’t match our current mission. 
Within two weeks we then narrowed it down to these three more Startup-friendly strategy planning tools for team sizes of 8+.

If you’re wondering what strategy really means, here’s a “strategy intro“ post by consultant jim babb:

Think of strategy as a map. You’re here, but you need to be there. A good strategy lets you pick the best route while dodging dead-ends and detours.

OnStrategy — bulldozer of strategy planning

It’s a browser based software that walks you through your SWOT, mission, vision and goals. Like every other tool it then asks for your goals and KPIs to keep track and measure performance. Their app helped me to add new goals and team items but it’s not doing so well when you need an overall view/reporting while on the road. Their tooltips and questions around each topic help you to focus. If you need more help, then OnStrategy offers consultants to guide you (I haven’t tested it yet) — from $300 to $5,000. 
Startup fit/lean: okay/good
User Interface/Usability: **** of *****
The thread: OnStrategy’s forms sometimes make you write endless strategy descriptions and makes you build a lot of Action Items. You’ll have to prioritize them on your own. 
What it could do better: Connecting goals, SWOT and team strategy to sling everything together. Planning cascade is really missing (or I haven’t seen it). 
Why it helped: It made me thinking that too many tasks adn goals were on my very own table. it helped me to delegate team goals and action items.
Pricing: $100 for self service (OnStrategy is just not making this visible) and $500/month for a more enterprise feel, 14 day trial time (and when you do a call, it will extend to 40 days 
Conclusio: With this price-set they’re not an option for Startups anymore.

Envisio — attention to details

Envisio focuses on strategy execution. It sits at the end of the strategy process and build its platform on goals and the performance overview. They offered us demo calls and we really felt accompanied by a human (not a bot). Envisio’s blog does an okay job to keep you up-to-date with all-strategy related topics. 
Startup fit/lean: okay (municipals and enterprises are their customers)
User Interface/Usability: currently testing
The thread: currently testing
What it could do better: visualization, reporting 
Why it helped: currently testing 
Pricing: They only tell you after their demo call. It starts at around $4,500/year for 20 users included. 
Conclusio: still in progress

Cascade — transparency and team

The Australian software company with offices on almost every continent helps very much with setting up the planning process and useful content around strategy. 
The software, mainly focusing on enterprises than startups, is showing individual employees exactly how their tasks contribute to a workplace’s strategy. That’s what I missed at OnStrategy and Envisio. 
I continuously browse their blog to learn from others (“8 CEOs about strategy” is my fav). They’re very supportive and keen to learn from their user’s behavior. My onboarding call with Carl was a great intro and made me feel, Cascade is the right tool for planning, measuring and achieving our strategic goals.
Here’s a link to their ebook (you normally have to subscribe to get that). You can also book a 30 min. demo which I’ll review soon. 
TechCrunch reviewed the tool, too.
Startup fit/lean: okay/good
User Interface/Usability: *** of ***** -none of the tested platforms were abel to achieve a 4-star UI rating. Stragey is a beast and all the tools are still overwhelming in terms of UI. 
The thread: try to avoid a deep 4-level-planning. Personally I think such tools should not try to become Jira for software. 
What it could do better: more context how each form & item helps you to achieve your overall organization and team goal.
Why it helped: Cascade emphasizes transparency by allowing users to see everyone else’s data. More important: It connects your vision to goals.
Pricing: about $60/month for a team of 4 ($16/month/user), 14 days trial time. If you provide valuable feedback, Cascade might be extending your trial. 
Conclusio: Looks like an alternative to OnStrategy.

We ended up here after applying strategic planning with Cascade:

Avoid Pitfalls

While sometimes using such tools is like using a sledgehammer to crack a nut, it really helps you in a more mature and later stage phase of your startup. Nevertheless these are traps you should avoid while adding your strategy to one of the reviewed software tools:

1. Never consider forming a strategy as lightweight (although it’s not difficult).
2. Understand the Planning Architecture before you begin. Otherwise you’ll get lost.
3. Include your team and discuss almost every outcome. Use it as a process to align the team and spread motivation.
4. Don’t avoid conflict! Avoid consensus and drive a healthy discussion, discover your team’s opinion.
5. Simple language. We added too many special terms which the team barely understood to the first strategy draft. 
   Accessibility is key. Making the strategy fun, relevant and not overly complex.
6. Strategic vs operational: Just don’t mix these two. An operational plan defines the day-to-day activities of your organization over a specified (often annual) time frame that enable the implementation of the strategies.
7. Not every goal or task has a KPIs. Limit your KPIs (key performance indicator) to only those numbers that really matter. I’D recommend only 3–4 KPIs for the overall company review. It doesn’t that you set KPIs for team members or rather entire teams.
8. Don’t overthink strategy! Think of it as a roadmap to get you where you want to be. But, don’t make it up as you go and fly by the seat of your pants or you’ll end up with a reactive strategy rather than a proactive plan. Your goal is simple: Reach the right audience with the right message at the right time, but strategy isn’t a set-it-and-forget-it process. It takes nurturing, adjusting and tracking.

Nevertheless, these tools won’t help you find your sweet spot, nor they’ll find your biggest challenges and solve them. You need an entire tool-set to create value with your Startup. 
Other strategic planning tools we’re using at Compass.to for finding the right business model or aligning the team are:

• Business Model Canvas. I’d recommend the Strategyzer training. Although it can get really ugly when applying this methodology at your startup. It can be time consuming but ultimately helpful. Before applying this, you should assign someone (I think it’s always a CEO’s job) to be on top of how the Business Model Canvas works. It took us several attempts and fails until we’ve figured out how the Canvas really helps. Now we’ve implemented this deeply in our team-thinking and -structure.
• SWOT Analysis
• Customer Journey Map

Now what?

If execution of your strategy planning is sound, implementing systems that can increase efficiency and accuracy may be your next step. I wouldn’t recommend using OnStrategy or Cascade for implementing the strategy in tech heavy and agile teams.

I’d be happy to share knowledge with everyone who’s looking to discuss best startup and execution strategies: “steve (at) compass.to”, meet me on LinkedIn.