Dakota doesn’t replace a great tutor or counselor. It amplifies your value, gives you a deeper understanding of every student—and creates more time to act on it.
“I asked Dakota to look across a student’s last 30 days of assignments and show me exactly where the recurring speed issues are. That is far more useful than simply knowing they ran out of time on one test.”
— Chandler Waggoner, SAT/ACT tutor and college advisor
98 Questions to Ask Dakota
Workspace 1: Test Prep
Prepare for the Next Session
- “Review Sally’s work since our session last week. Which assignments did she complete, and which did she leave unfinished?”
- “Compare Sally’s accuracy and pace before and after her last two Algebra assignments. What improved, and what still needs teaching?”
- “Tom has a 60-minute session today and his SAT is in 30 days. Which two Standard English Conventions subskills should we prioritize?”
- “Create a 60-minute session plan for Leo: 15 minutes reteaching his weakest subskill, 25 minutes of guided practice and a 20-minute mastery check.”
- “Based on Ava’s last three assignments, what should I teach, practice with her and assign independently next?”
- “What has changed in Maya’s work since our last session that should change what I planned to teach today?”
- “What should I ask Leo at the start of today’s session to quickly check whether he retained what we covered last time?”
Understand Past Performance
Dakota can look across the learner model—not just at one test or assignment.
- “Analyze Daniel’s last 30 days across coverage, accuracy, speed and mastery. Identify the three biggest constraints on his score.”
- “Which SAT Math subskills has Priya not yet covered? Rank them by likely score impact.”
- “Across Jordan’s last five assignments, which traps recur most often in Advanced Math, and how many times did each appear?”
- “Sam runs out of time in the second Math module. Which question types are slowing him down the most, and how far above target pace is he?”
- “Find the hard Reading and Writing questions Alex answers correctly but takes more than 90 seconds to complete. Group them by subskill.”
- “Which of Ella’s previously secure Geometry and Trigonometry skills have started to slip in her last 30 days of work?”
- “Maya has scored around 1320 on three tests. Is her plateau driven by coverage, accuracy, speed, mastery—or a combination? What are you seeing?”
- “Jordan is scoring 760 in Math. Which subskills, traps or timing issues should we focus on if he is trying to reach an 800?”
- “If Tom could fix only three subskills before his next test, which would create the greatest score opportunity—and why?
- “How did Leo do on his latest test? What improved, what should we focus on next, and which questions should we review in our next session?”
- “Which Advanced Math skills does Maya answer correctly at medium difficulty but miss at hard difficulty?”
- “Which improvements in Priya’s recent work look like real progress, and which might just be a one-off?”
Create Personalized Assignments
This is where Dakota turns analysis into action.
- “Create a mixed review assignment for Sally that combines recently learned skills with older skills she may be starting to forget.”
- “Review Tom’s Standard English Conventions performance from the last 30 days. Which subskills does he miss most? Create three hard questions for each subskill.”
- “Find the hard Reading and Writing questions Alex gets right but takes more than 90 seconds to answer. Create a 15-question timed assignment targeting those question types.”
- “Which Geometry and Trigonometry skills has Ella learned but not retained? Create three hard questions per skill to rebuild mastery.”
- “Compare Priya’s last two Bluebook tests. Create her next assignment around the three highest-priority skills to work on.”
- “Create a 12-question high-difficulty Math assignment targeting the skills and traps Jordan most needs to work on next.”
- “Prepare Sally’s Advanced Math assignment, schedule it to appear in her To-Do list after school and make it due before our next session.”
- “Create a 20-minute assignment for Maya that focuses on her highest-priority skills without overloading her before our next session.”
Turn Wrong Answers into Learning
- “Create homework for Daniel to review the mistakes from his latest Bluebook test that are most important to understand before our next session.”
- “Have Priya review the mistakes from her latest test and sort them by what went wrong: didn’t know how, made a mistake, ran out of time, or was careless.”
- “For each Standard English Conventions question Tom missed, ask him to explain why his choice was wrong and why the correct answer is supported.”
- “Review Maya’s missed Advanced Math questions one at a time. Give her one hint at a time and identify where her reasoning goes off track.”
- “Classify each of Sally’s 14 missed questions by domain, subskill, difficulty and error type.”
- “Create two similar hard questions for each recurring trap Daniel identified in his wrong-answer review.”
- “For the questions Ella missed, which ones does she seem to understand but still get wrong, and which ones point to a real knowledge gap?”
- “Which errors could Jordan still not explain after guided review, and which ones should I teach directly?”
- “Which of Ava’s mistakes are new, and which are patterns she has made before?”
- “What does Priya think caused each mistake, and does that match what her work shows?”
Use Dakota During a Session
- “Tom missed this boundaries question. Which punctuation rule is involved, and what diagnostic question should I ask him first?”
- “Explain this nonlinear equation to Sally in a different way; the algebraic explanation did not land.”
- “Show Alex a faster way to solve this hard Advanced Math question, and compare it with the approach he used.”
- “Create one medium and one hard question using this same subskill so I can check whether Maya can transfer what she learned.”
- “Sally solved this hard question correctly. Make the next one harder so I can see whether she can apply the skill in a more challenging problem.”
- “Give Jordan an unfamiliar version of this functions question that would challenge a student targeting an 800 in Math.”
- “Tom knew the grammar rule but selected the wrong answer. Is this a knowledge problem or an execution problem?”
- “Using Maya’s history and today’s answers, has she shown enough mastery of quadratics to move on? What are you seeing?”
- “Priya is stuck on this question. What hint should I give her without giving away the answer?”
- “Maya is getting frustrated with this problem. What should I ask or show her next without taking over the thinking?”
Extend Tutoring Between Sessions:
- “Sally has 25 minutes before school tomorrow. Which assignment should I have her complete based on the plan we made?”
- “Create a short review for Leo to reinforce what we covered in today’s session before we meet again.”
- “Have Daniel retry the questions he missed today later this week so I can see what he retained.”
- “At the end of Priya’s homework, ask her what still feels confusing and save those questions for our next session.”
- “What should Ava practice independently this week, and what should I wait to work on with her in our next session?”
- “If Leo gets stuck while working independently, help him work through it without giving him the answer and flag where he needed help for me.”
- “Before our next session, summarize what Maya completed, where she struggled and what she asked Dakota for help with.”
Communicate with Parents
- “Create a parent-friendly report for Sally’s last 30 days covering assignments completed, coverage, accuracy, speed, mastery and next steps.”
- “Tom has remained around 1320 across three tests. Explain the plateau to his parent using concrete examples from his work.”
- “Explain to Jordan’s parents what is still holding him back in Math despite a 760 score, including timing on hard questions and recurring traps.”
- “Show Priya’s parents three improvements that may not show up in her total score yet and two areas we are still working on.”
- “Draft a five-sentence post-session update: what we covered, what Sally mastered, her homework, when it is due and our next focus.”
- “Compare Daniel’s baseline with his last 30 days and summarize for his parents where he has improved, where he is still struggling, and what that means for his next steps—using coverage, accuracy, speed and mastery.”
- “Explain Maya’s next two-week plan without technical language: the goals, scheduled assignments and what we will focus on in tutoring.”
- “Draft a response to Ava’s parents explaining whether she is on track for her target score, what is improving, and what still needs work.”
- “Draft a response to a parent who is concerned that their child is working hard but their test score has not improved yet.”
Workspace 2: College Research
Understand the Student Through Thrive
- “Explain this student’s Thrive Report to me.”
- “What does this student need from a college environment to thrive?”
- “Which findings should we explore more deeply in our session?”
- “Which colleges best match this student’s Thrive Report—and why?”
- “Where does their current college list seem misaligned with what matters most in their Thrive Report?”
- “Compare these two colleges for this student based on the factors that matter most in their Thrive Report.”
- “Is there a type of college or campus environment we should add to their list based on their Thrive Report?”
- “Which parts of this student’s Thrive Report should carry the most weight as we build their college list?”
- “What questions should I ask this student to understand which Thrive findings actually matter most to them?”
Conduct and Assign Better College Research
- “Research how this university is incorporating AI into the student’s intended subject.”
- “Research the undergraduate opportunities at this college that are most relevant to this student’s interests and goals.”
- “Prepare me for my college-list session: summarize where the current list is strong, where there may be gaps, and which schools we should discuss.”
- “Create an assignment for the student to investigate whether this university is a good fit for them.”
- “Create a research assignment on the academic program they want to discuss in their supplement.”
- “What should this student investigate before writing their ‘Why Us?’ essay?”
- “The student is drawn to this college for its small classes, collaborative culture and strength in their intended major. Research whether those impressions hold up and flag anything we should discuss.”
Workspace 3: Application Coach
Help the Counselor Improve the Personal Statement
- “What are the three most important ways this student could improve their personal statement?”
- “What is the strongest idea in this personal statement, and what is competing with it?”
- “What is an admissions reader likely to learn about this student from the essay?”
- “Where is the student spending too much time describing what happened and not enough time reflecting on why it mattered?”
- “Is the structure helping or weakening the story?”
- “Is this a personal statement—or a résumé disguised as an essay?”
- “Does this essay sound like the student?”
- “Where does the language feel generic or overly polished?”
- “What questions should I ask the student in our session to help them go deeper in this personal statement?”
- “Compare these two drafts. What improved?”
- “Create a revision assignment based on today’s discussion.”
Strengthen the Complete Application
- “Could this ‘Why Us?’ essay be sent to five other colleges?”
- “Does the supplement connect the university research to this particular student?”
- “What does the application currently communicate clearly about this student’s strengths, interests and character?”
- “What important part of the student’s story or identity is still missing from the application?”
- “Are the essays repeating what is already clear from the activities list instead of revealing something new about the student?”
- “What are the two or three strongest themes an admissions reader is likely to take away from the application as a whole?”
- “Do the different essays feel like they were written by the same student?”
- “Looking across the essays, activities and academic profile, is anything inconsistent or left unexplained?”
Useful Platform Functions
These are practical platform functions—not Ask Dakota or AI features.
- Assign and track homework.
- Schedule or reschedule sessions.
- View every student on one calendar.
- Message students between sessions.
- Message parents and share reports.
- See sessions, assignments, messages and progress in one place for each student.
The Bottom Line
Dakota does the analysis, remembers what happened and helps students keep moving between sessions. Tutors and counselors bring the judgment, relationships and coaching that turn that intelligence into progress.