Leadership development, connected to real work

See what is getting in the way. Decide what to do next.

DearestWatson connects short assessments, real work, and AI coaching in one shared evidence base. Leaders get a practical next step. Team leaders and organisation administrators see patterns without exposing individual responses.

Try Play to Win See how it works

10 questions · about 5 minutes · no sign-in · demo results are not saved

A clear signal. Short assessments connected to real situations.

One useful move. Coaching close to the decision or conversation.

A review. See what changed without monitoring individuals.

Inside the product

See the platform at work

Complete a short assessment built around one recognisable leadership situation.

View the related capability →

DevelopmentLeadership growth

Your development path

Leadership growth

A focused path built around one real development goal.

✓Goal

✓Starting
point

3Focus

4Lessons

5Progress
check

6Review

The brief

Development goalBecome ready for a more senior or strategic scope of responsibility

AudienceIndividual

Readiness evidence

Connect immediate choices to a longer-term direction
Make consequential decisions with incomplete information
Align stakeholders around priorities and trade-offs

WatsonAI coach

Grounded in your evidence

Prepare the conversation

Watson keeps the relevant assessment and development context in view.

Help me prepare for the decision meeting. I need us to leave with a clear owner.

Your evidence suggests that you can carry a decision too long before involving others. Open by naming the decision, then ask who needs to shape it before you choose.

ⓘ Why this advice? · Decision Gravity

Give me the exact opening.

“We need to decide who owns this today. Before I propose an answer, what needs to be true for the owner to succeed?”

Ask Watson about this situation

Team dysfunctions03 / 10

Which answer is closer?

When thinking about collaboration between functions, which answer is closer?

← Previous question

InsightFull-screen results

Person lens

Jens Tav

Consultant · HR Development

Assessment results

GROW coaching model20 May 2026

Reflective Listener

The pattern puts most emphasis on understanding the person’s current reality through listening and questions.

What this says about this person

You appear willing to slow the conversation down and let the other person make sense of their situation.

From insight to a change you can review

Notice the pattern

Maja sees that she tends to carry decisions too long before involving her team.

Try one useful move

Before the next meeting, Watson suggests sharing the decision frame before sharing the answer.

Review what changed

Afterwards, she records what shifted. Her team leader sees the team pattern, not Maja’s private response.

One connected system, not separate tools

Built from more than 30 years of leadership practice, DearestWatson keeps the evidence, coaching, and follow-up together. Open a capability to see the product itself.

EU data residency

Your DearestWatson data stays in the EU.

Your information is kept within the EU. The platform and its database are hosted in Stockholm, AI features use Mistral’s European endpoint, and essential emails are sent through LetterMint in Amsterdam.

You can access, correct, export, or erase your data directly in the product. For more detail about our providers and data handling, contact info@dearestwatson.com.

Your data is stored in Stockholm

Supabase · Stockholm, Sweden

Your profile, assessments, and results are stored in Stockholm, with access limited to the right people in your organisation.

The platform is hosted in Stockholm

Vercel · Stockholm, Sweden

The DearestWatson application is hosted in Vercel’s Stockholm region.

AI processing stays in the EU

Mistral AI · European Union

AI-powered features use Mistral’s European endpoint, so the information needed for each request is processed in the EU.

Essential emails are sent from Amsterdam

LetterMint · Amsterdam, Netherlands

Invitations and essential account emails are delivered through LetterMint’s European infrastructure in Amsterdam.

One evidence base. A different view for each role.

Participants work with their own evidence. Team leaders can access only the teams they lead. Organisation administrators work across their own organisation. Aggregate team patterns remain separate from named individual views.

Participant

A development path built around real work, not a generic course

Watson, an AI coach grounded in their own evidence

Fast, mobile-friendly assessments, signed in via SSO or a secure invite

Team leader

Aggregate team patterns, plus permitted named scores and dynamics for the teams they lead

Meeting Intelligence and Stakeholder Match, the same tools organisation administrators use

Can start a development path for anyone on their team

Organisation administrator

People and team administration in one organisation workspace

Organisation-wide named and aggregate insight within their permitted scope

Full control over the roster, team leaders, and administrator access

Different responsibilities, without separate systems or duplicate data.

Colleagues working together in a Danish office

Microsoft workspace

Works within the Microsoft environment your organisation already uses

Use DearestWatson in the browser or Microsoft Teams. IT retains control of identity and access through Microsoft Entra ID, with SAML sign-in and SCIM provisioning.

Work in Microsoft Teams

DearestWatson in Teams

A personal tab and bot bring relevant coaching and development work into Teams.

Meeting Intelligence in Teams

For supported scheduled meetings, Microsoft Graph supplies the completed transcript. When that option is unavailable, people can use the in-panel recorder with explicit consent.

Keep identity and access in IT

SAML single sign-on

Connect Microsoft Entra ID or another compatible identity provider, and manage access policy centrally.

SCIM provisioning

Synchronise joiners and leavers so access follows your organisation’s existing process.

Bring one real leadership challenge

We will show you how DearestWatson turns it into a signal, a practical move and a way to review what changed. If the platform is not a fit, we will say so.

Talk to us

Why DearestWatson exists

Leadership development should leave evidence of what changed

DearestWatson holds two things together: a structured record of how a leader works, and a coach that turns it into language and actions they can use.

50+

Structured leadership and team assessments in one evidence library

30+

Years of leadership practice behind the method

In plain terms

Evidence comes from assessments, meetings, and everyday work. Watson turns it into coaching, team insight, and reporting from the same shared foundation.

Many leadership tools hand over a diagnosis and stop there. DearestWatson keeps the development work going after the assessment, so a leader can use a focused lesson in real work and review whether it changed the pattern.

Watson works from a person’s permitted evidence and their organisation’s verified context, and identifies which source shaped each answer. Access runs through the organisation using SSO or a secure invitation. There is no public sign-up.

Shubhada Watson

Founder and creator of @DearestWatson
MCP · M.Sc. · Massachusetts Institute of Technology (MIT)

Why @DearestWatson

The name comes from two places: my own lived experience in this field, and Sherlock Holmes’s indispensable Watson—the loyal companion who makes things clearer not through genius, but by asking the right question at the right moment. That is what this is built to be.

After more than 30 years working across leadership, culture diagnoses, organisational reviews, and personal coaching, I kept seeing the same gap between the assessment and the outcome. Generative AI made it possible to carry the useful part of that work into the next real decision, meeting, or conversation: small enough to use and structured enough to review.

"Knowing is not enough; we must apply. Willing is not enough; we must do."

Johann Wolfgang von Goethe, quote from his book 'Wilhelm Meister's Journeyman Years', 1829

Five ways organisations use it

Leadership development

A cohort works through a sequence of assessments, and each participant gets a focused development path with short lessons applied in real work and Watson coaching against their own evidence between sessions. What changed is reviewed, not assumed, so the path stays honest.

Team insight

A team leader gets a current view of their own team as evidence arrives. Aggregate patterns support the team conversation, while permitted named scores and dynamics remain limited to the teams they lead. Raw individual answers are not presented as team evidence.

Turn a recorded meeting into clearer follow-up

For a supported transcript or an explicitly consented recording, Watson reviews the intended outcome, dynamics, decisions, and follow-up actions against the words that were actually used.

Stakeholder Match

Start with the work or start with the person. A client, hiring manager, or project sponsor describes what success looks like, and Watson shows which person, team, or group best fits the need. Alternatively, begin with an individual and discover where they are most likely to work well. Six purposes are supported: project delivery, ongoing collaboration, manager relationships, mentoring, advisory work, and joining a team.

Organisation review

One workspace covers people and teams, with individual, team, and organisation-wide views built for real leadership conversations. Organisation administrators can see where capabilities are thin and how a population has moved since the last cycle. The view supports development planning and is deliberately not built to rank individuals.

Trust and access

There is no open sign-up. Organisations are set up with a workspace, and participants join through SSO or a secure invitation. Personal development remains the participant’s own space. Team leaders can access only the teams they lead; organisation administrators remain limited to their own organisation.

What the platform does

Supports reflection, coaching conversations, and development planning.

What it does not do

Automated employment, compensation, clinical, or legal decisions.

Where the data lives

Application compute and production data in Stockholm, AI processing in the EU, and transactional email in Amsterdam.

Questions about data or eligibility: info@dearestwatson.com

Bring one current leadership challenge. We will show you what the platform would do with it, and say clearly if it is not a fit.

Start a conversation →

Straightforward pricing

One plan. The full platform is included.

350 DKK per person per month, billed annually. For more flexibility, choose monthly billing at 500 DKK per person per month. There is no setup fee or feature tiers, and we configure the workspace with your organisation.

The full platform

Every capability is included from the start.

No setup fee

Workspace configuration and onboarding are included.

Start at a useful scale

Begin with one group and expand when the model works.

350 DKK / person / month

Annual agreement

Full assessment library and Watson AI coach
Team insight included
Single sign-on (SAML) and SCIM provisioning
Onboarding support, no setup fee
EU-based hosting and data processing

Talk to us about fit

For larger organisations, we can agree volume pricing. Write to info@dearestwatson.com.

Usage included with every seat

Monthly capacity is pooled across the workspace, so it can follow where the work is happening.

6,000 Watson coaching messages

1,000 minutes of meeting recording and analysis

100 Stakeholder Match analyses

Included allowance per seat, shared across the workspace. The mix can vary by team.

Start with a small group. Expand when it is useful.

We set up the workspace with you, including access, roles, and the first development path. A wider rollout can follow once the approach is useful and clear.

Agree the scope

Choose the people, the leadership question and which capabilities should be available.

Connect access

Use your organisation’s SSO and provisioning, or begin with secure email invitations.

Invite the group

Participants begin with short, mobile-friendly assessments and a clear explanation of privacy.

Review the evidence

Use individual and aggregated views to decide what to continue, change, or stop.

PWA available now. The native iOS app is built and awaiting Apple App Store approval.

Start a conversation

Tell us what you are trying to understand or improve. A person reads every note and replies with a walkthrough or a direct answer about fit.

Prefer email? info@dearestwatson.com

We use what you send only to understand the request and scope a possible workspace. We do not add you to a marketing list.

Questions

Can anyone sign up?

No. DearestWatson is purchased and managed by organisations. People join through your SSO or a secure invitation. There is no consumer sign-up and no free tier.

Is it a chatbot?

No. Watson coaches from a person’s own assessment evidence and tracked commitments rather than open conversation, and it identifies which lens shaped an answer. The chat surface is one way to reach the coaching layer, not the product itself.

Does it make automated employment decisions?

No. Insight is for development and reflection. It is not designed or licensed for automated employment, compensation, clinical, or legal decisions. Organisation-wide views show aggregated, not individual, data.

Where does our data live?

DearestWatson’s production service is EU-based: Vercel application compute and the Supabase production database run in Stockholm, AI requests use Mistral’s EU endpoint, and LetterMint handles transactional email in Amsterdam.